Herbicidal N-hydroxy-N&#39;-sulfonylguanidines

ABSTRACT

Novel N-hydroxy-N&#39;-sulfonylguanidine compounds are described which possess significant herbicidal and plant growth regulant activity for control of undesired vegetation.

This application is a divisional of my copending application Ser. No.060,212, filed Jun. 10, 1987, now U.S. Pat. No. 4,750,930, which is adivisional of Ser. No. 736,950, filed May 22, 1985, now issued as U.S.Pat. No. 4,689,070, which is a continuation-in-part of Ser. No. 551,381,filed Nov. 17, 1983, now abandoned, which is a continuation-in-part ofSer. No. 455,504, filed Jan. 4, 1983, now abandoned.

BACKGROUND OF THE INVENTION

This invention relates to certain novel N-hydroxy-N'-sulfonylguanidinecompounds, to compositions containing such compounds, and to a method ofuse of such compositions to control the growth of undesired vegetation.

U.S. Pat. No. 4,127,405 issued Nov. 28, 1978 discloses substitutedtriazinyl arylsulfonylurea compounds of the following formula: ##STR1##while U.S. Pat. No. 4,169,719 issued Oct. 2, 1979 discloses substitutedpyrimidinyl arylsulfonylurea compounds of the following formula:##STR2## The triazine and pyrimidine compounds within the scope of the'405 and '719 patents include those wherein W can be oxygen or sulfur.

U.S. Pat. No. 4,310,346 issued Jan. 12, 1982 disclosessulfonylisothiourea compounds of the formula ##STR3## wherein B is C₁-C₆ alkyl, CH₂ CH₂ OCH₃, CH₂ CH₂ OCH₂ CH₃, CH₂ CH₂ CH₂ OCH₃, CH₂ Q,##STR4## where Q is CO₂ -C₁₋₃ alkyl, ##STR5## phenyl, phenyl substitutedwith chlorine, CN, C₂₋₄ alkenyl, C₂₋₄ alkynyl, OR₁₁, where R₁₁ is C₁ -C₄alkyl, --CH₂ OCH₂ CH₂ OCH₃ or --CH₂ OCH₂ CH₂ OCH₂ CH₃.

South African Pat. No. 79/2657, published Jun. 30, 1980 disclosessulfonylisothiourea compounds of the formula ##STR6## wherein R₂ is C₁-C₂₀ alkyl; CH₂ CH₂ OCH₃ ; CH₂ CH₂ OCH₂ CH₃ ; CH₂ CH₂ CH₂ OCH₃ ; CH₂ OA'where A' is C₁ -C₁₂ alkyl, --CH₂ CH₂ OCH₃, --CH₂ CH₂ OCH₂ CH₃, phenyl orphenyl substituted with 1-2 NO₂, 1-2 Cl, or 1-2 CH₃ ; CH₂ A, ##STR7##where A is CO₂ (H, C₁ -C₄ alkyl), ##STR8## phenyl, CN, C₂ -C₄ alkenyl,C₁ -C₄ alkynyl, phenyl substituted with 1-2 CH₃, 1-2 NO₂, 1-2 OCH₃, 1-2chlorine or phenoxy.

U.S. Pat. No. 4,301,286 issued Nov. 17, 1981 disclosesO-alkylsulfonylisoureas of the formula ##STR9## wherein W is Cl, Br orOR¹² ; and

R¹² is C₁ -C₁₂ alkyl, C₃ -C₄ alkenyl, CH₂ CH₂ OCH₃, CH₂ CH₂ OCH₂ CH₃,(CH₂)₃ OCH₃, benzyl, CHR¹³ CO₂ R¹⁴, where R¹³ is H or CH₃ and R¹⁴ is C₁-C₄ alkyl.

South African patent application No. 84/4808 discloses herbicidalsulfonamides of formula ##STR10## wherein R₁ is a phenyl or phenoxygroup; each of

R₂ and R₃ is a lower alkyl or lower alkoxy group; and

R₄ is a hydrogen atom, a lower alkyl group or a lower alkoxy group.

The compounds taught in the above references are useful as general orselective herbicides having both preemergent and postemergent herbicidalactivity or plant growth regulant activity.

SUMMARY OF THE INVENTION

The novel sulfonylguanidine compounds of the present inventionincorporating a guanidyloxyl moiety are highly active herbicides in bothpreemergent and postemergent applications. Certain compoundsadditionally exhibit selective herbicidal safety to wheat and barley.Specifically, the invention relates to novel compounds of formula I,agriculturally suitable compositions containing them and theirmethod-of-use as pre-emergent and/or post-emergent herbicides or plantgrowth regulants. ##STR11## wherein R is H or CH₃ ;

R' is OH, OC(O)R₁, OC(O)NR₂ R₃, OCOR₄, OR₃ or R₃ ;

R₁ is C₁ -C₃ alkyl or CF₃ ;

R₂ is H, CH₃ or C₂ H₅ ;

R₃ is C₁ -C₃ alkyl;

R₄ is C₁ -C₃ alkyl;

L is ##STR12## R₅ is C₁ -C₄ alkyl, C₁ -C₄ alkoxy, OCH₂ CH₂ OCH₃, F, Cl,Br, NO₂, CF₃, CO₂ R₁₉, SO₂ NR₂₀ R₂₁, SO₂ N(OCH₃)CH₃, OSO₂ R₂₂, S(O)_(n)R₂₃, WCF₃, WCHF₂, C₃ -C₄ alkenyloxy, C₃ -C₄ alkynyloxy, C₁ -C₂ alkylsubstituted with OCH₃ or OCH₂ CH₃, C₆ H₅, ##STR13## R₆ is H, F, Cl, Br,CF₃, CH₃, OCH₃, SCH₃ or OCF₂ H;

R₇ is H, CH₃, OCH₃, F, Cl, Br, SO₂ N(CH₃)₂, OSO₂ CH₃ or S(O)_(n) CH₃ ;

R₈ is CH₃, CH₂ CH₃, OCH₃, OCH₂ CH₃, F, Cl, Br, SO₂ NR₂₀ R₂₁, SO₂N(OCH₃)CH₃ or S(O)_(n) R₂₃ ;

R₉ is C₁ -C₃ alkyl, F, Cl, Br, NO₂, CO₂ R₁₉, SO₂ NR₂₀ R₂₁, SO₂N(OCH₃)CH₃ or S(O)_(n) R₂₃ ;

R₁₀ is Cl, NO₂, CO₂ CH₃, CO₂ CH₂ CH₃, SO₂ N(CH₃)₂, OSO₂ CH₃, SO₂ CH₃,SO₂ CH₂ CH₃, OCH₃ or OCH₂ CH₃ ;

R₁₁ is H, CH₃ or CH₂ CH₃ ;

R₁₂ is H, CH₃ or CH₂ CH₃ ;

R₁₃ is H or CH₃ ;

R₁₄ is H or CH₃ ;

R₁₅ is H or CH₃ ;

R₁₆ is CH₃ or CH₂ CH₃ ;

R₁₇ is H or C₁ -C₄ alkyl;

R₁₈ is H or CH₃ ;

R₁₉ is C₁ -C₄ alkyl, CH₂ CH₂ OCH₃, CH₂ CH₂ Cl or CH₂ CH═CH₂ ;

R₂₀ is C₁ -C₃ alkyl;

R₂₁ is C₁ -C₃ alkyl;

R₂₂ is C₁ -C₃ alkyl or N(CH₃)₂ ;

R₂₃ is C₁ -C₃ alkyl or CH₂ CH═CH₂ ;

m is 0 or 1;

n is 0 or 2;

Q₁ is O, S, SO₂ or NR₁₇ ;

Q₂ is O, S or NR₁₇ ; and

W is O, S or SO₂ ;

A is ##STR14## X is CH₃, OCH₃, OCH₂ CH₃, Cl, F, Br, OCF₂ H, CH₂ F or CF₃;

Y is H, CH₃, OCH₃, OCH₂ CH₃, CH₂ OCH₃, CH₂ OCH₂ CH₃, N(CH₃)₂, CH₂ CH₃,CF₃, SCH₃, OCH₂ CH═CH₂, OCH₂ C.tbd.CH, OCH₂ CF₃, OCH₂ CH₂ OCH₃, CH₂SCH₃, OCF₂ H, SCF₂ H, CR₂₄ (QCH₃)₂, ##STR15## or CR₂₄ (QCH₂ CH₃)₂ ; Q isO or S;

R₂₄ is H or CH₃ ;

Z is CH or N;

Y₁ is CH₂ or O;

X₁ is CH₃, OCH₃, OCH₂ CH₃ or OCF₂ H;

Y₂ is H or CH₃ ;

X₂ is CH₃, CH₂ CH₃ or CH₂ CF₃ ;

Y₃ is OCH₃, OCH₂ CH₃, SCH₃, CH₃ or CH₂ CH₃ ;

X₃ is CH₃ or OCH₃ ;

provided that

(1) the total number of carbon atoms of R₂₀ and R₂₁ is less than orequal to four;

(2) when m is 1, then R₁₃ is H;

(3) when L is L-17, then R₁₇ and R₁₈ are not simultaneously H;

(4) when X is Cl, F or Br, then Z is CH and Y is OCH₃, OCH₂ CH₃, N(CH₃)₂or OCF₂ H;

(5) when R' is C₁ -C₃ alkoxy or C₁ -C₃ alkyl, and L is L-1 then eitherR₅ is other than C₆ H₅ or R₆ is other than H; and

(6) when X or Y is OCF₂ H, then Z is CH.

This invention also relates to novel compounds of Formula II, suitableagricultural compositions containing them and their method of use asgeneral or selective preemergent or postemergent herbicides or plantgrowth regulants. ##STR16## wherein R" is C₁ -C₃ alkyl;

R, L and A are defined for Formula I;

provided that

(1) when L is L-1 and A is A-1, R₅ is C₂ -C₄ alkyl, C₂ -C₄ alkoxy, OCH₂CH₂ OCH₃, OSO₂ R₂₂, S(O)_(n) CH₂ CH═CH₂, WCF₂, WCHF₂, C₃ -C₄ alkenyloxy,C₃ -C₄ alkynyloxy, C₁ -C₂ alkyl substituted with OCH₃ or OCH₂ CH₃, C₆H₅, ##STR17## (2) when L is L-1 and A is A-2 or A-3, then R₅ is C₂ -C₄alkyl, C₂ -C₄ alkoxy, OCH₂ CH₂ OCH₃, OSO₂ R₂₂, WCF₃, WCHF₂, C₃ -C₄alkenyloxy, C₃ -C₄ alkynyloxy, C₁ -C₂ alkyl substituted with OCH₃ orOCH₂ CH₃, C₆ H₅, ##STR18## (3) when L is L-3 and A is A-1, A-2 or A-3,then R₈ is SO₂ NR₂₀ R₂₁, SO₂ N(OCH₃)CH₃ or SO₂ R₂₃ ;

(4) when L is L-4, L-5 or L-6 and A is A-1, A-2 and A-3, then R₉ is C₁-C₃ alkyl, F, Cl, Br, NO₂, SO₂ NR₂₀ R₂₁, SO₂ N(OCH₃)CH₃ or S(O)_(n) R₂₃; and

(5) when L is L-2, then A is A-5 or A-6.

Preferred for reasons of their higher herbicidal activity, greater plantgrowth regulant activity or more favorable ease of synthesis are:

(1) Compounds of Formula I where R is H, R' is OH and A is A-1.

(2) Compounds of Formula I where R is H, R' is C₁ -C₂ alkoxy and A isA-1.

(3) Compounds of Preferred 1 where Y is CH₃, OCH₃, OCH₂ CH₃, CH₂ OCH₃,OCH₂ CF₃ or CH(OCH₃)₂ and X is CH₃, OCH₃, Cl or CF₃.

(4) Compounds of Preferred 2 where Y is CH₃, OCH₃, OCH₂ CH₃, CH₂ OCH₃,OCH₂ CF₃ or CH(OCH₃)₂ and X is CH₃, OCH₃, Cl or CF₃.

(5) Compounds of Preferred 3 where L is L-1, L-2, L-3, L-5, L-8, L-10,L-11, L-16 or L-17.

(6) Compounds of Preferred 5 where L is L-1, R₅ is OCH₃, OCH₂ CH₃, Cl,NO₂, CF₃, CO₂ CH₃, CO₂ CH₂ CH₃, SO₂ N(CH₃)₂, SO₂ N(OCH₃)CH₃, OSO₂ R₂₂,S(O)_(n) R₂₃, OCF₂ H, SCF₂ H, C₆ H₅, OCH₂ CH═CH₂, OCH₂ C.tbd.CH.##STR19## R₂₂ is C₁ -C₃ alkyl; R₂₃ is CH₃ and n is 2.

(7) Compounds of Preferred 4 where L is L-1, L-2, L-3, L-5, L-8, L-10,L-11, L-16 or L-17.

(8) Compounds of Preferred 7 where L is L-1, R₅ is OCH₃, OCH₂ CH₃, Cl,NO₂, CF₃, CO₂ CH₃, CO₂ CH₂ CH₃, SO₂ N(CH₃)₂, SO₂ N(OCH₃)CH₃, OSO₂ R₂₂,S(O)_(n) R₂₃, OCF₂ H, SCF₂ H, C₆ H₅, OCH₂ CH═CH₂, OCH₂ C.tbd.CH,##STR20## R₂₂ is C₁ -C₃ alkyl; R₂₃ is CH₃ and n is 2.

(9) Compounds of Preferred 5 where L is L-2 and R₇ is Cl, CH₃, OCH₃,SCH₃ or Br.

(10) Compounds of Preferred 5 where L is L-3 and R₈ is Cl, SO₂ CH₃ orSO₂ N(CH₃)₂.

(11) Compounds of Preferred 5 where L is L-5 and R₉ is CO₂ CH₃ or CO₂CH₂ CH₃.

(12) Compounds of Preferred 5 where L is L-8.

(13) Compounds of Preferred 5 where L is L-10.

(14) Compounds of Preferred 5 where L is L-11.

(15) Compounds of Preferred 5 where L is L-16.

(16) Compounds of Preferred 5 where L is L-17.

(17) Compounds of Preferred 7 where L is L-2 and R₇ is Cl, CH₃, OCH₃,SCH₃ or Br.

(18) Compounds of Preferred 7 where L is L-3 and R₈ is Cl, SO₂ CH₃ orSO₂ N(CH₃)₂.

(19) Compounds of Preferred 7 where L is L-5 and R₉ is CO₂ CH₃ or CO₂CH₂ CH₃.

(20) Compounds of Preferred 7 where L is L-8.

(21) Compounds of Preferred 7 where L is L-10.

(22) Compounds of Preferred 7 where L is L-11.

(23) Compounds of Preferred 7 where L is L-16.

(24) Compounds of Preferred 7 where L is L-17.

(25) Compounds of Formula II where R is H and A is A-1.

(26) Compounds of Preferred 25 where Y is CH₃, OCH₃, OCH₂ CH₃, CH₂ OCH₃,OCH₂ CF₃ or CH(OCH₃)₂ and X is CH₃, OCH₃, Cl or CF₃ ;

(27) Compounds of Preferred 26 where L is L-1 and R₅ is OSO₂ R₂₂, SO₂CH₂ CH═CH₂, OCF₂ H, SCF₂ H, OCH₂ CH═CH₂, OCH₂ C.tbd.H, ##STR21## or C₆H₅.

Specifically Preferred for reasons of their highest herbicidal activityor greatest plant growth regulant activity or most favorable ease ofsynthesis are:

2-[[1-(4,6-dimethylpyrimidin-2-yl)amino]-1-(hydroxyimino)methyl]aminosulfonyl]benzoicacid methyl ester;

2-[[1-(4-methoxy-6-methylpyrimidin-2-yl)amino]-1-(hydroxyimino)methyl]aminosulfonyl]benzoicacid methyl ester;

N',N'-dimethyl-N-[[1-(4,6-dimethyl-1,3,5-triazin-2-yl)amino]-1-(hydroxyimino)methyl]-1,2-benzenedisulfonamide;

N',N'-dimethyl-N-[[1-(4-methoxy-6-methylpyrimidin-2-yl)amino]-1-(hydroxyimino)methyl]-1,2-benzenedisulfonamide;

3-chloro-N-[[1-(4,6-dimethoxypyrimidin-2-yl)amino]-1-[methoxyimino]methyl][1,1'-biphenyl]-2-sulfonamide;

N-[[1-(4,6-dimethoxy-1,3,5-triazin-2-yl)amino]-1-[methoxyimino]methyl]-3-methoxy[1,1'-biphenyl]-2-sulfonamide;and

N-[[1-(4,6-dimethylpyrimidin-2-yl)amino]-1-(hydroxyimino)methyl]-2-chlorobenzenesulfonamide,m.p. 165-167.

DETAILED DESCRIPTION OF THE INVENTION

Synthesis

The compounds of Formula Ia may be prepared by the reaction ofhydroxylamine with an appropriately substituted S-alkyl benzenesulfonylisothiourea of Formula II, as shown in Equation 1.

Equation 1 ##STR22## wherein L, R, R" and A are as previously defined.

The reaction of Equation 1 is conducted by contacting 1-3 equivalents ofhydroxylamine hydrochloride and an equivalent amount of sodium acetatewith a compound of Formula II in a suitable solvent, such astetrahydrofuran, at 0°-30° for 1-24 hours. The product may be isolatedby removal of solvent and trituration of the residue with water.

The compounds of Formula II may be prepared by the methods described inU.S. Pat. No. 4,301,286 and are herein incorporated by reference.Alternatively, they may be prepared by the procedure outlined inEquation 2.

Equation 2 ##STR23## wherein L, R, R" and A are as previously defined.

The reaction of Equation 2 may be carried out by contacting a sulfonylchloride of Formula III with an appropriately substituted S-alkylisothiourea of Formula IV in an inert solvent, such as methylenechloride or tetrahydrofuran, in the presence of an acid scavenger, suchas aqueous sodium bicarbonate or a tertiary amine, such astriethylamine, for 1-3 days at 20°-40°. The product is isolated byremoval of solvent and trituration of the residue with water, or byextraction from water with an organic solvent, concentration, andchromatography.

Reference to the following patents and patent applications is suggestedfor details regarding the preparation of the sulfonyl chlorides III:U.S. Pat. No. 4,169,719, U.S. Pat. No. 4,127,405; U.S. Pat. No.4,383,113; U.S. Pat. No. 4,394,506; U.S. Pat. No. 4,120,691; U.S. Pat.No. 4,238,621; European patent application No. 80304286.0, publishedJun. 10, 1981; European patent application No. 79302769.9, publishedJul. 23, 1980; Canadian Pat. No. 1128042; European patent applicationNo. 82301500.3, published Nov. 17, 1982; European patent application No.81305160.4, published May 12, 1982; and copending U.S. patentapplication Ser. No. 410,993, filed Aug. 27, 1982; U.S. patentapplication Ser. No. 406,191, filed Aug. 11, 1982, U.S. patentapplication Ser. No. 499,443, filed May 31, 1983 and U.S. patentapplication Ser. No. 436,631, filed Oct. 10, 1982.

The preparation of the compounds of Formula IV is shown in Equations 3,4 and 5.

Equation 3 ##STR24## wherein R, R" and A are as previously defined.

The reaction of Equation 3a may be carried out by saturation of asolution of a compound of Formula V in pyridine with hydrogen sulfide,allowing to react for 1 to 5 days at 25° to 40°, removal of pyridine invacuo, and crystallization of the product with water or an organicsolvent such as ether or methylene chloride. The resulting compound ofFormula VI may be reacted according to Equation 3b with one equivalentof a dialkyl sulfate or alkyl iodide at 20° to 80° for 1 to 3 days toprovide the corresponding alkyl sulfate or iodide salt of IV. The freebase may be obtained by extraction from aqueous sodium bicarbonate withan organic solvent, such as ethyl acetate. An alternative synthesis ofcompounds of Formula VI is shown in Equation 4.

Equation 4 ##STR25## wherein R and A are as previously defined; and J isC₆ H₅ or C₆ H₅ O.

The reaction of Equation 4a is carried out by contacting a compound ofFormula VII with 1-1.5 equivalents of benzoyl- orphenoxycarbonylisothiocyanate at 30°-80° for 1-24 hours in a suitablesolvent, such as acetonitrile or tetrahydrofuran. The product may beisolated by cooling or concentration and filtration. The reaction ofEquation 4b may be performed by heating the compound of Formula VIII inan aqueous medium, with or without a cosolvent, in the presence of 1 to2 equivalents of an alkali metal hydroxide or an alkali earth oxide at30° to 80° for 1-24 hours. The product is isolated by cooling,neutralization to pH 8, and filtration in the case where an alkali metalhydroxide is used, and in the case where an alkali earth oxide is used,the reaction mixture is filtered and the filtrate is concentrated,cooled, and filtered.

Heterocyclic amines of Formula VII and methods for preparing them areknown in the art. The synthesis of heterocyclic amines such as those ofFormula VII has been reviewed in "The Chemistry of HeterocyclicCompounds", a series published by Interscience Publ., N.Y. and London.2-Aminopyrimidines are described by D. J. Brown in "The Pyrimidines",Vol. XVI of this series. 2-Amino-1,3,5-triazines can be preparedaccording to methods described by E. M. Smolin and L. Rapaport in"s-Triazines and Derivatives", Vol. XIII of the same series. Thesynthesis of triazines is also described by F. C. Schaefer, U.S. Pat.No. 3,154,547 and by K. R. Huffman and F. C. Schaefer; J. Org. Chem.,28, 1816 (1963). See also U.S. patent application Ser. No. 434,038,filed Oct. 20, 1982, European patent application No. 80300505.7,published Sept. 17, 1980 (Pub. No. 15,683), European patent applicationNo. 81303837.9, published Mar. 3, 1982 (Pub. No. 46,677); Europeanpatent application No. 82306492.8, published Jul. 27, 1983 (Pub. No.84,224); and European patent application No. 82303611.6, published Mar.9, 1983 (Pub. No. 73,562), for description of methods for preparingheterocyclic amine derivatives.

A third method by which certain compounds of Formula IV may be obtainedis shown in Equation 5.

Equation 5 ##STR26## wherein R, R", X and Y are as previously defined.

The reaction of Equation 5 may be carried out by contacting achlorotriazine of Formula IX with an S-alkyl isothiourea of Formula X inthe same manner as was described in the reaction of Equation 2.

Compounds of Formulae Ib and Ic may be obtained from those of Formula Iaby the reactions of Equation 6.

Equation 6 ##STR27## wherein R^(a) is C(O)R₁, C(O)NR₂ R₃, or CO₂ R₄, andL, R, R₁, R₂, R₃, R₄, and A are as previously defined.

The reaction of Equation 6a is carried out by contacting Ia with 1-10equivalents of the appropriate carboxylic acid chloride or anhydride, oralkyl chloroformate, or dialkyl carbamoyl chloride in the presence of anacid scavenger, such as pyridine or a tertiary amine, at 0° to 40° for 2to 24 hours, adding ice-water, and filtering or extracting the productinto an organic solvent.

The reaction of Equation 6b may be conducted by treating a solution ofIa in an inert solvent such as methylene chloride or acetonitrile with1-1.5 equivalents of an alkyl isocyanate at 20°-80° for 1 to 24 hours.The product is isolated by concentrating the reaction mixture andtrituration with a solvent such as ether or chlorobutane.

Additional methods for preparation of compounds of this invention aredescribed in South African patent application 84/4808.

Agriculturally suitable salts of compounds of Formulae I and II are alsouseful herbicides. Salts of compounds of Formulae I and II can beprepared in a number of ways known to the art. For example, metal saltscan be made by treating compounds of Formulae I and II with a solutionof an alkali or alkaline earth metal salt having a sufficiently basicanion (e.g., hydroxide, alkoxide, carbonate or hydride). Quaternaryamine salts can be made by similar techniques.

Salts of compounds of Formulae I and II can also be prepared by exchangeof one cation for another. Cationic exchange can be effected by directtreatment of an aqueous solution of a salt of a compound of Formulae Iand II (e.g., alkali metal or quaternary amine salt) with a solutioncontaining the cation to be exchanged.

This method is most effective when the desired salt containing theexchanged cation is insoluble in water, e.g., a copper salt, and can beseparated by filtration.

Exchange may also be effected by passing an aqueous solution of a saltof a compound of Formulae I and II (e.g., an alkali metal or quaternaryamine salt) through a column packed with a cation exchange resincontaining the cation to be exchanged. In this method, the cation of theresin is exchanged for that of the original salt and the desired productis eluted from the column. This method is particularly useful when thedesired salt is water-soluble, e.g., a potassium, sodium or calciumsalt.

Acid addition salts, useful in this invention, can be obtained byreacting a compound of Formulae I and II with a suitable acid, e.g.,p-toluenesulfonic acid, trichloroacetic acid or the like. Thedisclosures of all references cited above are herein incorporated byreference.

In the following examples, all parts are by weight and temperatures in°C. unless otherwise indicated.

EXAMPLE 12-Chloro-N-[[(4,6-dimethylpyrimidin-2-yl)amino]hydroxyiminomethyl]benzenesulfonamide

To a solution of 0.5 g of methylN'-(2-chlorophenylsulfonyl)-N-(4,6-dimethylpyrimdin-2-yl)carbamimidothioatein 10 ml of tetrahydrofuran was added 0.3 g of hydroxylaminehydrochloride and 0.3 g of sodium acetate. The mixture was stirred atroom temperature for 2 hours, whereupon the product was precipitatedwith ice-water, filtered, washed with water, and dried by suction toafford 0.3 g of the title compound, m.p. 165°-167°. NMR(CDCl₃ /DMSO-d₆)δ2.6 (s, 6), 6.8 (s, 1), 7.4 (m, 3), 8.2 (m, 1), 10.2 (br, 1), 12.0 (br,1). m/e: 355 (M⁺).

EXAMPLE 2 N-(4,6-Dimethylpyrimidin-2-yl)thiourea

A suspension of 10 g of 2-cyanoamino-4,6-dimethylpyrimidine in 50 ml ofpyridine was saturated with hydrogen sulfide and stored for 1 hour at25°. The H₂ S treatment was repeated twice more, and the mixture wasallowed to stir at 25° for 16 hours. Methylene chloride was added, andthe product was filtered and washed with methylene chloride to afford 8g of 4,6-dimethylpyrimidin-2-yl thiourea, m.p. >260°. IR (Nujol) 3280,3180, 3120, 1610 cm⁻¹.

EXAMPLE 3N-[(4-Methoxy-6-methylpyrimidin-2-yl)aminothioxomethyl]benzamide

To a hot solution of 14 g of ammonium thiocyanate in 300 ml ofacetonitrile was added 24 ml of benzoyl chloride. The mixture was heatedon the steam bath for 30 minutes and filtered. The filtrate was heatedwith 21 g of 4-methoxy-6-methylpyrimidine-2-amine for 30 minutes andcooled. The product was collected by filtration and washed with a littleacetonitrile to provide 28 g ofN-[[(4-methoxy-6-methylpyrimidin-2-yl)aminothiocarbonyl]amino]benzamide,m.p. 193°-195°. IR (Nujol) 3290, 1720 cm⁻¹.

EXAMPLE 4 N-(4-Methoxy-6-methylpyrimidin-2-yl)thiourea

A mixture of 25 g of the compound from Example 3 and 55 ml of 10%aqueous sodium hydroxide was heated on the steam bath for 30 minutes,cooled, neutralized with aqueous HCl to pH 8, filtered, washed withwater, dried by suction, and washed with ether to afford 16 g of thetitle compound, m.p. 220° d.

Anal. Calc'd.: C: 42.4, H: 5.06, N: 28.2, S: 16.2 Found: C: 42.6, H:4.8, N: 28.8, S: 15.3 m/e 198 (M⁺).

EXAMPLE 5 Methyl2-[[1-(4-methoxy-6-methylpyrimidin-2-ylimino)-1-(methylthio)methyl]aminosulfonyl]benzoate

To 9 g of the compound from Example 4 and 100 ml of tetrahydrofuran wasadded 7.6 g of dimethyl sulfate and the mixture was stirred for 2 daysat room temperature. The product was filtered and washed with a littletetrahydrofuran to give 22 g of crude product. Five grams of thismaterial was suspended in 150 ml of methylene chloride and 1 ml ofwater, and 5 g of sodium bicarbonate and 6 g of methyl 2-chlorosulfonylbenzoate were added. The mixture was stirred for 24 hours, washed withdilute aqueous HCl, dried with sodium sulfate, filtered, andchromatographed on silica gel to afford 2.8 g of the title compound as acrystalline solid, m.p. 143°-144°.

Anal. Calc'd.: C: 45.22, H: 4.55, N: 14.06, S: 16.1 Found: C: 46.8, H:4.35, N: 13.2, S: 16 m/e 395 (M⁺ --CH₃),

NMR(CDCl₃) δ2.35 (s, 3), 2.45 (s, 3), 3.90 (s, 3), 4.0 (s, 3) 6.35 (s,1), 7.7 (m, 3), 8.2 (m, 1), 10.8 (brs. 1).

EXAMPLE 6 Methyl N-(4,6-dimethoxy-1,3,5-triazin-2-yl)carbaminidothioate

A mixture of 20 g of 2-chloro-4,6-dimethoxy-s-triazine, 20 g of S-methylisothiouronium sulfate, 16 g of sodium carbonate, and 50 ml of water wasstirred for 72 hours, concentrated at reduced pressure, and extractedwith 300 ml of methylene chloride. The organic layer was dried with Na₂SO₄, filtered, concentrated to dryness, and recrystallized fromchlorobutane to afford 10 g of title compound, m.p. 94°-100°. NMR(CDCl₃)δ2.6 (s, 3), 4.0 (s, 6), 8.2 (brs, 1).

Using the procedures and examples shown above, the compounds in Tables1-13 can be prepared.

                                      TABLE 1a                                    __________________________________________________________________________     ##STR28##                                                                    R.sub.5 R.sub.6                                                                            R"  R  X   Y        m.p. (°C.)                            __________________________________________________________________________    SCH.sub.2 CHCH.sub.2                                                                  3-Cl CH.sub.3                                                                          H  OCH.sub.3                                                                         OCH.sub.3                                             SCH.sub.2 CHCH.sub.2                                                                  H    C.sub.2 H.sub.5                                                                   H  OCH.sub.3                                                                         OC.sub.2 H.sub.5                                      OSO.sub.2 .sub.--n-C.sub.3 H.sub.7                                                    H    CH.sub.3                                                                          CH.sub.3                                                                         CH.sub.3                                                                          CH.sub.2 OCH.sub.3                                    OSO.sub.2 .sub.--n-C.sub.3 H.sub.7                                                    H    CH.sub.3                                                                          H  CH.sub.3                                                                          SCH.sub.3                                             OSO.sub.2 CH.sub.3                                                                    H    CH.sub.3                                                                          H  OCH.sub.3                                                                         CH.sub.3                                              OSO.sub.2 CH.sub.3                                                                    H    CH.sub.3                                                                          H  OCH.sub.3                                                                         OCH.sub.3                                             CH.sub.2 CH.sub.3                                                                     5-Br CH.sub.3                                                                          H  CH.sub.3                                                                          OCH.sub.3                                             CH.sub.2 CH.sub.3                                                                     H    CH.sub.3                                                                          H  CH.sub.3                                                                          CH.sub.3                                               .sub.--n-C.sub.4 H.sub.9                                                             H     .sub.--n-C.sub.3 H.sub.7                                                         H  OCH.sub.3                                                                         OCH.sub.3                                              .sub.-i-C.sub.3 H.sub.7                                                              H    CH.sub.3                                                                          CH.sub.3                                                                         OCH.sub.3                                                                         CH.sub.3                                              OSO.sub.2 N(CH.sub.3).sub.2                                                           H    CH.sub.3                                                                          H  CH.sub.3                                                                          CH(OCH.sub.2 CH.sub.2 O)                              OCH.sub.2 CH.sub.3                                                                    H    CH.sub.3                                                                          H  CH.sub.3                                                                          CH.sub.3                                              OCH.sub.2 CH.sub.3                                                                    H    CH.sub.3                                                                          H  CH.sub.3                                                                          OCH.sub.3                                             O .sub.-i-C.sub.3 H.sub.7                                                             H    CH.sub.3                                                                          H  OCH.sub.3                                                                         OCH.sub.3                                             O .sub.-i-C.sub.3 H.sub.7                                                             H    CH.sub.3                                                                          H  OCH.sub.3                                                                         C.sub.2 H.sub.5                                       O .sub.--n-C.sub.4 H.sub.9                                                            H    CH.sub.3                                                                          H  CH.sub.3                                                                          CH(OCH.sub.3).sub.2                                   O .sub.--n-C.sub.4 H.sub.9                                                            H    CH.sub.3                                                                          H  CH.sub.3                                                                          OC.sub.2 H.sub.5                                      SO.sub.2 CF.sub.2 H                                                                   5-CH.sub.3                                                                         CH.sub. 3                                                                         H  OCH.sub.3                                                                         OCH.sub.3                                             SO.sub.2 CF.sub.2 H                                                                   H    C.sub.2 H.sub.5                                                                   H  OCH.sub.3                                                                         OC.sub.2 H.sub.5                                      SCF.sub.2 H                                                                           6-SCH.sub.3                                                                        CH.sub.3                                                                          CH.sub.3                                                                         CH.sub.3                                                                          CH.sub.2 OCH.sub.3                                    SCF.sub.2 H                                                                           H    CH.sub.3                                                                          H  CH.sub.3                                                                          SCH.sub.3                                             OCF.sub.3                                                                             H    CH.sub.3                                                                          H  OCH.sub.3                                                                         CH.sub.3                                              OCF.sub.3                                                                             H    CH.sub.3                                                                          H  OCH.sub.3                                                                         OCH.sub.3                                             CH.sub.2 OCH.sub.3                                                                    H     .sub.--n-C.sub.3 H.sub.7                                                         H  OCH.sub.3                                                                         OCH.sub.3                                             CH.sub.2 OCH.sub.3                                                                    H    CH.sub.3                                                                          CH.sub.3                                                                         OCH.sub.3                                                                         CH.sub.3                                              CH.sub.2 OCH.sub.2 CH.sub.3                                                           H    CH.sub.3                                                                          H  Cl  OCH.sub.3                                             CH.sub.2 OCH.sub.2 CH.sub.3                                                           H    CH.sub.3                                                                          H  Cl  CH.sub.3                                              OCF.sub.2 H                                                                           H    CH.sub.3                                                                          H  OCH.sub.3                                                                         CH.sub.3                                              OCF.sub.2 H                                                                           H    CH.sub.3                                                                          H  CH.sub.3                                                                          CH(OCH.sub.2 CH.sub.2 O)                              __________________________________________________________________________

                                      TABLE 1b                                    __________________________________________________________________________     ##STR29##                                                                    R.sub.5   R.sub.6                                                                            R"  R  X   Y        m.p. (°C.)                          __________________________________________________________________________    SO.sub.2 CH.sub.2 CHCH.sub.2                                                            H    CH.sub.3                                                                          H  OCH.sub.3                                                                         OCH.sub.3                                           SO.sub.2 CH.sub.2 CHCH.sub.2                                                            H    CH.sub.3                                                                          H  OCH.sub.3                                                                         C.sub.2 H.sub.5                                     OSO.sub.2 .sub.--n-C.sub.3 H.sub.7                                                      H    CH.sub.3                                                                          CH.sub.3                                                                         CH.sub.3                                                                          CH.sub.2 OCH.sub.3                                  OSO.sub.2 .sub.--n-C.sub.3 H.sub.7                                                      H    CH.sub.3                                                                          H  CH.sub.3                                                                          SCH.sub.3                                           OSO.sub.2 CH.sub.3                                                                      H    CH.sub.3                                                                          H  OCH.sub.3                                                                         CH.sub.3                                            OSO.sub.2 CH.sub.3                                                                      H    CH.sub.3                                                                          H  OCH.sub.3                                                                         OCH.sub.3                                           CH.sub.2 CH.sub.3                                                                       3-Br CH.sub.3                                                                          H  CH.sub.3                                                                          OCH.sub.3                                           CH.sub.2 CH.sub.3                                                                       H    CH.sub.3                                                                          H  CH.sub.3                                                                          CH.sub.3                                             .sub.--n-C.sub.4 H.sub.9                                                               H     .sub.--n-C.sub.3 H.sub.7                                                         H  OCH.sub.3                                                                         OCH.sub.3                                            .sub.-i-C.sub.3 H.sub.7                                                                H    CH.sub.3                                                                          CH.sub.3                                                                         OCH.sub.3                                                                         CH.sub.3                                            OSO.sub.2 N(CH.sub.3).sub.2                                                             H    CH.sub.3                                                                          H  CH.sub.3                                                                          CH(OCH.sub.2 CH.sub.2 O)                            OCH.sub.2 CH.sub.3                                                                      H    CH.sub.3                                                                          H  CH.sub.3                                                                          CH.sub.3                                            OCH.sub.2 CH.sub.3                                                                      H    CH.sub.3                                                                          H  CH.sub.3                                                                          OCH.sub.3                                           O .sub.-i-C.sub.3 H.sub.7                                                               H    CH.sub.3                                                                          H  OCH.sub.3                                                                         OCH.sub.3                                           O .sub.-i-C.sub.3 H.sub.7                                                               H    CH.sub.3                                                                          H  OCH.sub.3                                                                         C.sub.2 H.sub.5                                     O .sub.--n-C.sub.4 H.sub.9                                                              H    CH.sub.3                                                                          H  CH.sub.3                                                                          CH(OCH.sub.3).sub.2                                 O .sub.--n-C.sub.4 H.sub.9                                                              H    CH.sub.3                                                                          H  CH.sub.3                                                                          OC.sub.2 H.sub. 5                                   SO.sub.2 CF.sub.2 H                                                                     6-SCH.sub.3                                                                        CH.sub.3                                                                          H  OCH.sub.3                                                                         OCH.sub.3                                           SO.sub.2 CF.sub.2 H                                                                     H    C.sub.2 H.sub.5                                                                   H  OCH.sub.3                                                                         OC.sub.2 H.sub.5                                    SCF.sub.2 H                                                                             H    CH.sub.3                                                                          CH.sub.3                                                                         CH.sub.3                                                                          CH.sub.2 OCH.sub.3                                  SCF.sub.2 H                                                                             H    CH.sub.3                                                                          H  CH.sub.3                                                                          SCH.sub.3                                           OCF.sub.3 H    CH.sub.3                                                                          H  OCH.sub.3                                                                         CH.sub.3                                            OCF.sub.3 H    CH.sub.3                                                                          H  OCH.sub.3                                                                         OCH.sub.3                                           CH.sub.2 OCH.sub.3                                                                      H     .sub.--n-C.sub.3 H.sub.7                                                         H  OCH.sub.3                                                                         OCH.sub.3                                           CH.sub.2 OCH.sub.3                                                                      H    CH.sub.3                                                                          CH.sub.3                                                                         OCH.sub.3                                                                         CH.sub.3                                            CH.sub.2 OCH.sub.2 CH.sub.3                                                             H    CH.sub.3                                                                          H  Cl  OCH.sub.3                                           CH.sub.2 OCH.sub.2 CH.sub.3                                                             H    CH.sub.3                                                                          H  Cl  CH.sub.3                                            OCF.sub.2 H                                                                             H    CH.sub.3                                                                          H  OCH.sub.3                                                                         CH.sub.3                                            OCF.sub.2 H                                                                             H    CH.sub.3                                                                          H  OCH.sub.3                                                                         OCH.sub.3                                           OCF.sub.2 H                                                                             H    CH.sub.3                                                                          H  CH.sub.3                                                                          CH.sub.3                                            CH.sub.2 CH.sub.2 OC.sub.2 H.sub.5                                                      H    CH.sub.3                                                                          H  OCH.sub.3                                                                         CH.sub.3                                            __________________________________________________________________________

                                      TABLE 1c                                    __________________________________________________________________________     ##STR30##                                                                                                           m.p.                                   R" R  R.sub.5   R.sub.6                                                                            X   Y          Z  (°C.)                           __________________________________________________________________________    CH.sub.3                                                                         H  OCH.sub.2 CH.sub.2 OCH.sub.3                                                            H    CH.sub.3                                                                          H          CH                                        CH.sub.3                                                                         H  OCH.sub.2 CHCH.sub.2                                                                    H    CH.sub.3                                                                          CH.sub.3   N                                         CH.sub.3                                                                         H  OCH.sub.2 CHCH                                                                          6-OCH.sub.3                                                                        CH.sub.3                                                                          CH.sub.3   CH                                        CH.sub.3                                                                         H  C.sub.6 H.sub.5                                                                         H    CH.sub.3                                                                          CH.sub.3   N                                         CH.sub.3                                                                         H                                                                                 ##STR31##                                                                              H    CH.sub.3                                                                          OCH.sub.3  CH                                        CH.sub.3                                                                         H                                                                                 ##STR32##                                                                              H    OCH.sub.3                                                                         OCH.sub.3  N                                         CH.sub.3                                                                         H                                                                                 ##STR33##                                                                              H    OCH.sub.3                                                                         OCH.sub.2 CCH                                                                            N                                         CH.sub.3                                                                         H                                                                                 ##STR34##                                                                              H    OCH.sub.3                                                                         OCH.sub.2 CH.sub.2 OCH.sub.3                                                             N                                         CH.sub.3                                                                         H  C.sub.2 H.sub.5                                                                         H    OCH.sub.3                                                                         OCF.sub.2 H                                                                              CH                                        CH.sub.3                                                                         H  OCF.sub.3 H    OCH.sub.3                                                                         SCF.sub.2 H                                                                              CH                                        CH.sub.3                                                                         H  SO.sub.2 CH.sub.3                                                                       3-OCF.sub.2 H                                                                      OCH.sub.3                                                                         C(CH.sub.3)(OCH.sub.3).sub.2                                                             CH                                        CH.sub.3                                                                         H  OCH.sub.2 CH.sub.3                                                                      H    OCH.sub.3                                                                         CF.sub.3   N                                         CH.sub.3                                                                         H  SO.sub.2 CH.sub.2 CH.sub.3                                                              H    OCH.sub.3                                                                         N(CH.sub.3).sub.2                                                                        CH                                        CH.sub.3                                                                         CH.sub.3                                                                         SO.sub.2 CH.sub. 2 CH.sub.3                                                             H    OCH.sub.3                                                                         C(CH.sub.3)(SCH.sub.3).sub.2                                                             N                                         CH.sub.3                                                                         H  SO.sub.2 CH.sub.2 CH.sub.3                                                              H    OCF.sub.2 H                                                                       CH(SCH.sub.2 CH.sub.2 S)                                                                 CH                                        CH.sub.3                                                                         H  SO.sub.2 CH.sub.2 CH.sub.3                                                              H    CF.sub.3                                                                          CH.sub.2 CH.sub.3                                                                        CH                                        CH.sub.3                                                                         H  SO.sub.2 CH.sub.2 CH.sub.3                                                              H    F   OCH.sub.3  CH                                        CH.sub.3                                                                         H  SO.sub.2 CH.sub.2 CH.sub.3                                                              H    OC.sub.2 H.sub.5                                                                  C(CH.sub.3)(OCH.sub.2 CH.sub.2 O)                                                        CH                                        __________________________________________________________________________

                                      TABLE 1d                                    __________________________________________________________________________     ##STR35##                                                                                                                    m.p.                          R"  R  L                     X    Y          Z  (°C.)                  __________________________________________________________________________    CH.sub.3                                                                          H  L.sub.2 :R.sub.7 = Cl CH.sub.3                                                                           H          CH                               CH.sub.3                                                                          H  L.sub.2 :R.sub.7 = OCH.sub.3                                                                        CH.sub.3                                                                           CH.sub.3   CH                               CH.sub.3                                                                          H  L.sub.2 :R.sub.7 = SO.sub.2 N(CH.sub.3).sub.2                                                       CH.sub.3                                                                           CH.sub.3   CH                               CH.sub.3                                                                          H  L.sub.3 :R.sub.8 = SO.sub.2 N(CH.sub.3).sub.2                                                       CH.sub.3                                                                           CH.sub.3   CH                               CH.sub.3                                                                          H  L.sub.3 :R.sub.8 = SO.sub.2 CH.sub.3                                                                CH.sub.3                                                                           OCH.sub.3  CH                               CH.sub.3                                                                          CH.sub.3                                                                         L.sub.3 :R.sub.8 = SO.sub.2 CH.sub.2 CH.sub.3                                                       Cl   OCH.sub.3  CH                                .sub.-i-C.sub.3 H.sub.7                                                          H  L.sub.4 :R.sub.9 = Br OCH.sub.3                                                                          OCH.sub.3  CH                               CH.sub.3                                                                          H  L.sub.5 :R.sub.9 = C.sub.2 H.sub.5                                                                  OCH.sub.3                                                                          OCH.sub.2 CHCH.sub.2                                                                     CH                               CH.sub.3                                                                          H  L.sub.6 :R.sub.9 = Cl OCH.sub.3                                                                          OCH.sub.2 CCH                                                                            N                                CH.sub.3                                                                          H  L.sub.7 :R.sub.10 = CO.sub.2 CH.sub.3                                                               OCH.sub.3                                                                          OCH.sub.2 CF.sub.3                                                                       N                                CH.sub.3                                                                          H  L.sub.8 :Q.sub.1 = O, m = 0, R.sub.11 = R.sub.12 = R.sub.13 =                 CH.sub.3              OCH.sub.3                                                                          CH.sub.2 SCH.sub.3                                                                       CH                               CH.sub.3                                                                          H  L.sub.9 :Q.sub.2 = S, R.sub.14 = R.sub.15 = H                                                       OCH.sub.3                                                                          OCF.sub.2 H                                                                              CH                               CH.sub.3                                                                          H  L.sub.10 :m = 0, R.sub.13 = H, R.sub.16 = CH.sub.3                                                  OCH.sub.3                                                                          SCF.sub.2 H                                                                              CH                               CH.sub.3                                                                          H  L.sub.11 :m = 0, R.sub.13 = H                                                                       OCH.sub.3                                                                          C(CH.sub.3)(OCH.sub.3).sub.2                                                             CH                               CH.sub.3                                                                          H  L.sub.12 :m = 1, R.sub.13 = CH.sub.3                                                                OCH.sub.3                                                                          CF.sub.3   CH                               CH.sub.3                                                                          H  L.sub.13 :m = 0, R.sub.13 = H                                                                       OCH.sub.3                                                                          N(CH.sub.3).sub.2                                                                        CH                               CH.sub.3                                                                          CH.sub.3                                                                         L.sub.14 :R.sub.16 = CH.sub.2 CH.sub.3                                                              OCH.sub.3                                                                          C(CH.sub.3)(SCH.sub.3).sub.2                                                             CH                               CH.sub.3                                                                          H  L.sub.15 :R.sub.17 = CH.sub.3                                                                       OCF.sub.2 H                                                                        CH(SCH.sub.2 CH.sub.2 S)                                                                 CH                               CH.sub.3                                                                          H  L.sub.16 :R.sub.17 = H                                                                              CF.sub.3                                                                           CH.sub.2 CH.sub.3                                                                        CH                               CH.sub.3                                                                          H  L.sub.17 :R.sub.17 = R.sub.18 = CH.sub.3                                                            F    OCH.sub.3  CH                               CH.sub.3                                                                          H  L.sub.17 :R.sub.17 = R.sub.18 = CH.sub.3                                                            OC.sub.2 H.sub.5                                                                   C(CH.sub.3)(OCH.sub.2 CH.sub.2 O)                                                        CH                               __________________________________________________________________________

                                      TABLE 1e                                    __________________________________________________________________________     ##STR36##                                                                                                                     m.p.                         L                       R"  R  A                 (°C.)                 __________________________________________________________________________    L.sub.1 :R.sub.5 = CO.sub.2 CH.sub.3, R.sub.6 = H                                                     CH.sub.3                                                                          H  A.sub.4 :X.sub.1 = CH.sub.3, Y.sub.2 = H       L.sub.1 :R.sub.5 = SO.sub.2 CH.sub.3, R.sub.6 = H                                                     CH.sub.3                                                                          H  A.sub.5 :X.sub.2 = CH.sub.2 CH.sub.3,                                         Y.sub.3 = SCH.sub.3                            L.sub.1 :R.sub.5 = NO.sub.2, R.sub.6 = H                                                              CH.sub.3                                                                          H  A.sub.6 :X.sub.3 = OCH.sub.3                   L.sub.1 :R.sub.5 = Br, R.sub.6 = H                                                                    CH.sub.3                                                                          H  A.sub.3 :X.sub.1 = OCH.sub.3                   L.sub.1 :R.sub.5 = Cl, R.sub.6 = H                                                                    CH.sub.3                                                                          H  A.sub.5 :X.sub. 2 = CH.sub.3, Y.sub.3 =                                       OC.sub.2 H.sub.5                               L.sub.1 :R.sub.5 = C.sub.2 H.sub.5, R.sub.6 = H                                                       CH.sub.3                                                                          H  A.sub.2 :X.sub.1 = OCH.sub.3, Y.sub.1 = O      L.sub.1 :R.sub.5 = SCF.sub.3, R.sub.6 = H                                                             C.sub.2 H.sub.5                                                                   H  A.sub.3 :X.sub.1 = OCF.sub.2 H                 L.sub.17 :R.sub.17 = H, R.sub.18 = CH.sub.3                                                           CH.sub.3                                                                          H  A.sub.2 :X.sub.1 = OCH.sub.3, Y.sub.1 =                                       CH.sub.2                                       L.sub.16 :R.sub.17 = CH.sub.3                                                                         CH.sub.3                                                                          H  A.sub.3 :X.sub.1 = OCF.sub.2 H                 L.sub.2 :R.sub.7 = SCH.sub.3                                                                          CH.sub.3                                                                          H  A.sub.4 :X.sub.1 = CH.sub.3, Y.sub.2 =                                        CH.sub.3                                       L.sub.3 :R.sub.8 = F    CH.sub.3                                                                          H  A.sub.5 :X.sub.2 = CH.sub.2 CH.sub.3,                                         Y.sub.3 = OCH.sub.3                            L.sub.4 :R.sub.9 =  .sub.-i-C.sub.3 H.sub.7                                                           CH.sub.3                                                                          H  A.sub.5 :X.sub.2 = CH.sub.3, Y.sub.3 =                                        CH.sub.2 CH.sub.3                              L.sub.5 :R.sub.9 = SO.sub.2 CH.sub.3                                                                  CH.sub.3                                                                          H  A.sub.6 :X.sub.3 = OCH.sub.3                   L.sub.6 :R.sub.9 = SO.sub.2 CH.sub.3                                                                  CH.sub.3                                                                          H  A.sub.2 :X.sub.1 = OCH.sub.3, Y.sub.1 = O      L.sub.7 :R.sub.10 = OCH.sub.2 CH.sub.3                                                                CH.sub.3                                                                          H  A.sub.3 :X.sub.1 = CH.sub.3                    L.sub.8 :Q.sub.1 = S, R.sub.11 = R.sub.12 = CH.sub.3, m = 1, R.sub.13 =                               CH.sub.3                                                                          H  A.sub.6 :X.sub.3 = CH.sub.3                    L.sub.9 :Q.sub.2 = O, R.sub.14 = R.sub.15 = CH.sub.3                                                  CH.sub.3                                                                          H  A.sub.4 :X.sub.1 = OCH.sub.3, Y.sub.2 =                                       CH.sub.3                                       L.sub.10 :R.sub. 16 = C.sub.2 H.sub.5, R.sub.13 = CH.sub.3, m                                         CH.sub.3                                                                          H  A.sub.5 :X.sub.2 = CH.sub.3, Y.sub.3 =                                        SCH.sub.3                                      L.sub.11 :m = 1, R.sub.13 = H                                                                         CH.sub.3                                                                          H  A.sub.2 :X.sub.1 = CH.sub.3, Y.sub.1 =                                        CH.sub.2                                       L.sub.12 :m = 0, R.sub.13 = CH.sub.3                                                                  CH.sub.3                                                                          H  A.sub.2 :X.sub.1 = OCH.sub.3, Y.sub.1 =                                       CH.sub.2                                       L.sub.13 :m = 1, R.sub.13 = H                                                                         CH.sub.3                                                                          H  A.sub.5 :X.sub.2 = CH.sub.2 CF.sub.3,                                         Y.sub.3 = CH.sub.2 CH.sub.3                    L.sub.14 :R.sub.16 = CH.sub.3                                                                         CH.sub.3                                                                          H  A.sub.4 :X.sub.1 = OCH.sub.3, Y.sub.2 = H      L.sub.15 :R.sub.17 = CH.sub.3                                                                         CH.sub.3                                                                          H  A.sub.4 :X.sub.1 = OCH.sub.3, Y.sub.2 =        __________________________________________________________________________                                   H                                          

                                      TABLE 2A                                    __________________________________________________________________________     ##STR37##                                                                    R.sub.5   R.sub.6                                                                            R  R'      X   Y        m.p. (°C.)                      __________________________________________________________________________    Cl        H    H  OH      CH.sub.3                                                                          CH.sub.3 165-167°                        Cl        H    H  OH      CH.sub.3                                                                          OCH.sub.3                                                                              121-128°                        Cl        H    H  OH      OCH.sub.3                                                                         OC.sub.2 H.sub.5                                Cl        H    H  OH      OCH.sub.3                                                                         OCH.sub.3                                                                              142-144°                        F         H    H  OH      CH.sub.3                                                                          CH.sub.3                                        F         H    H  OH      CH.sub.3                                                                          OCH.sub.3                                       Br        H    H  OH      OCH.sub.3                                                                         CH.sub.3                                        Br        H    H  OH      OCH.sub.3                                                                         OCH.sub.3                                       NO.sub.2  H    H  OH      CH.sub.3                                                                          CH(OCH.sub.2 CH.sub. 2 O)                       NO.sub.2  H    CH.sub.3                                                                         OH      CH.sub.3                                                                          C.sub.2 H.sub.5                                 CF.sub.3  H    H  OH      OCH.sub.3                                                                         OC.sub.2 H.sub.5                                CF.sub.3  H    H  OH      OCH.sub.3                                                                         CH.sub.3                                        OCH.sub.3 H    H  OH      CH.sub.3                                                                          OCH.sub.3                                       OCH.sub.3 H    H  OH      CH.sub.3                                                                          CH(OCH.sub.3).sub.2                             OCH.sub.3 H    H  OH      Cl  CH.sub.3                                        OCH.sub.3 H    H  OH      Cl  OCH.sub.3                                       OC.sub.2 H.sub.5                                                                        H    H  OH      CH.sub.3                                                                          CH.sub.2 OCH.sub.3                              OC.sub.2 H.sub.5                                                                        H    H  OH      CH.sub.3                                                                          CH.sub.3                                        OC.sub.2 H.sub.5                                                                        H    CH.sub.3                                                                         OH      OCH.sub.3                                                                         OCH.sub.3                                       O .sub.-i-C.sub.3 H.sub.7                                                               H    H  OH      OCH.sub.3                                                                         CH.sub.3                                        O -n-C.sub.3 H.sub.7                                                                    H    H  OH      CH.sub.3                                                                          OCH.sub.3                                       O -n-C.sub.3 H.sub.7                                                                    H    H  OH      CH.sub.3                                                                          CH.sub.3                                        O .sub.-i-C.sub.4 H.sub.9                                                               H    H  OH      OCH.sub.3                                                                         OCH.sub.3                                       O .sub.-i-C.sub.4 H.sub.9                                                               H    H  OH      OCH.sub.3                                                                         CH.sub.3                                        CO.sub.2 CH.sub.3                                                                       H    H  OH      CH.sub.3                                                                          CH.sub.3 M.sup.+  = 379*                        CO.sub.2 CH.sub.3                                                                       H    H  OH      CH.sub.3                                                                          OCH.sub.3                                                                              M.sup.+ = 395*                         CO.sub.2 CH.sub.3                                                                       H    H  OH      OCH.sub.3                                                                         OC.sub.2 H.sub.5                                SO.sub.2 N(CH.sub.3).sub.2                                                              H    H  OH      OCH.sub.3                                                                         OCH.sub.3                                       SO.sub.2 N(CH.sub.3).sub.2                                                              H    H  OH      CH.sub.3                                                                          CH.sub.3                                        SO.sub.2 N(CH.sub.3).sub.2                                                              H    H  OH      CH.sub.3                                                                          OCH.sub.3                                                                              166-168°                        SO.sub.2 N(CH.sub.3).sub.2                                                              H    H  OH      OCH.sub.3                                                                         OCH.sub.2 CH.sub.3                              SO.sub.2 N(CH.sub.3).sub.2                                                              H    H  OH      CH.sub.3                                                                          CH(OCH.sub.2 CH.sub.2 O)                        SO.sub.2 N(CH.sub.2 CH.sub.3).sub.2                                                     H    CH.sub.3                                                                         OH      CH.sub.3                                                                          C.sub.2 H.sub.5                                 SO.sub.2 N(CH.sub.2 CH.sub.3).sub.2                                                     H    H  OH      OCH.sub.3                                                                         OC.sub.2 H.sub.5                                SO.sub.2 N(CH.sub.2 CH.sub.3).sub.2                                                     H    H  OH      OCH.sub.3                                                                         CH.sub.3                                        CO.sub.2 CH.sub.2 CH.sub.3                                                              H    H  OH      CH.sub.3                                                                          OCH.sub.3                                       CO.sub.2 CH.sub.2 CH.sub.3                                                              H    H  OH      CH.sub.3                                                                          CH(OCH.sub.3).sub.2                             CO.sub.2 CH.sub.3                                                                       H    H  OH      Cl  CH.sub.3                                        CO.sub.2 CH.sub.3                                                                       H    H  OH      Cl  OCH.sub.3                                       CO.sub.2 CH.sub.3                                                                       H    H  OH      CH.sub.3                                                                          CH.sub.2 OCH.sub.3                              CO.sub.2 .sub.-i-C.sub.3 H.sub.7                                                        H    H  OH      CH.sub.3                                                                          CH.sub.3                                        CO.sub.2 .sub.-i-C.sub.3 H.sub.7                                                        H    CH.sub.3                                                                         OH      OCH.sub.3                                                                         OCH.sub.3                                       SO.sub.2 N(OCH.sub.3)CH.sub.3                                                           H    H  OH      OCH.sub.3                                                                         CH.sub.3                                        CO.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3                                                    H    H  OH      CH.sub.3                                                                          OCH.sub.3                                       CO.sub.2 CH.sub.2 CHCH.sub.2                                                            H    H  OH      CH.sub.3                                                                          CH.sub.3                                        CO.sub.2 CH.sub.2 CH.sub.2 Cl                                                           H    H  OH      OCH.sub.3                                                                         OCH.sub.3                                       CO.sub.2 -n-C.sub.4 H.sub.9                                                             H    H  OH      OCH.sub.3                                                                         CH.sub.3                                        SO.sub.2 CH.sub.3                                                                       H    H  OH      CH.sub.3                                                                          CH.sub.3                                        SO.sub.2 CH.sub.3                                                                       H    H  OH      CH.sub.3                                                                          OCH.sub.3                                       SO.sub.2 CH.sub.3                                                                       H    H  OH      OCH.sub.3                                                                         OC.sub.2 H.sub.5                                SO.sub.2 CH.sub.3                                                                       H    H  OH      OCH.sub.3                                                                         OCH.sub.3                                       SO.sub.2 CH.sub.2 CHCH.sub.2                                                            H    H  OH      CH.sub.3                                                                          CH.sub.3                                        SO.sub.2 CH.sub.2 CHCH.sub.2                                                            H    H  OH      CH.sub.3                                                                          OCH.sub.3                                       SO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                     H    H  OH      OCH.sub.3                                                                         CH.sub.3                                        SCH.sub.2 CH.sub.3                                                                      H    H  OH      OCH.sub.3                                                                         OCH.sub.3                                       SCF.sub.3 H    H  OH      CH.sub.3                                                                          CH(OCH.sub.2 CH.sub.2 O)                        SO.sub.2 CHF.sub.2                                                                      H    CH.sub.3                                                                         OH      CH.sub.3                                                                          C.sub.2 H.sub.5                                 CH.sub.3  H    H  OH      OCH.sub.3                                                                         OC.sub.2 H.sub.5                                 .sub.-i-C.sub.3 H.sub.7                                                                H    H  OH      OCH.sub.3                                                                         CH.sub.3                                         -n-C.sub.4 H.sub.9                                                                     H    H  OH      CH.sub.3                                                                          OCH.sub.3                                       OSO.sub.2 N(CH.sub.3).sub.2                                                             H    H  OH      CH.sub.3                                                                          CH(OCH.sub.3).sub.2                             OSO.sub.2 N(CH.sub.3).sub.2                                                             H    H  OH      Cl  CH.sub.3                                        OSO.sub.2 CH(CH.sub.3).sub.2                                                            H    H  OH      Cl  OCH.sub.3                                       OSO.sub.2 C.sub.2 H.sub.5                                                               H    H  OH      CH.sub.3                                                                          CH.sub.2 OCH.sub.3                              OSO.sub.2 CH.sub.3                                                                      H    CH.sub.3                                                                         OH      OCH.sub.3                                                                         OCH.sub.3                                       OSO.sub.2 CH.sub.3                                                                      H    H  OH      OCH.sub.3                                                                         CH.sub.3                                        CH.sub.2 OCH.sub.3                                                                      H    H  OH      CH.sub.3                                                                          OCH.sub.3                                       CH.sub.2 CH.sub.2 OCH.sub.3                                                             H    H  OH      CH.sub.3                                                                          CH.sub.3                                        OCF.sub.3 H    H  OH      OCH.sub.3                                                                         OCH.sub.3                                       SO.sub.2 .sub.-i-C.sub.3 H.sub.7                                                        H    H  OH      OCH.sub.3                                                                         CH.sub.3                                        Cl        H    H  CH.sub.3 CO.sub.2                                                                     CH.sub.3                                                                          CH.sub.3 131-136° d                      Cl        5-CF.sub.3                                                                         H  OH      CH.sub.3                                                                          OCH.sub.3                                       Cl        H    H  CH.sub.3 OCO.sub.2                                                                    OCH.sub.3                                                                         OC.sub.2 H.sub.5                                Cl        6-SCH.sub.3                                                                        H  OH      OCH.sub.3                                                                         OCH.sub.3                                       F         5-SCH.sub.3                                                                        H  CH.sub.3 CO.sub.2                                                                     CH.sub.3                                                                          CH.sub.3                                        F         6-OCH.sub.3                                                                        H  OH      CH.sub.3                                                                          OCH.sub.3                                       Br        H    H  (CH.sub.3).sub.2 NCO.sub.2                                                            OCH.sub.3                                                                         CH.sub.3                                        Br        3-OCH.sub.3                                                                        H  OH      OCH.sub.3                                                                         OCH.sub.3                                       NO.sub.2  H    H  CH.sub.3 NHCO.sub.2                                                                   CH.sub.3                                                                          CH(OCH.sub.2 CH.sub.2 O)                        NO.sub.2  6-CH.sub.3                                                                         CH.sub.3                                                                         OH      CH.sub.3                                                                          C.sub.2 H.sub.5                                 CF.sub.3  5-CH.sub.3                                                                         H  CF.sub.3 CO.sub.2                                                                     OCH.sub.3                                                                         OC.sub.2 H.sub.5                                CF.sub.3  6-Cl H  C.sub.2 H.sub.5 CO.sub.2                                                              OCH.sub.3                                                                         CH.sub.3                                        OCH.sub.3 H    H  C.sub.2 H.sub.5 OCO.sub.2                                                             CH.sub.3                                                                          OCH.sub.3                                       OCH.sub.3 5-Cl H  OH      CH.sub.3                                                                          CH(OCH.sub.3).sub.2                             OCH.sub.3 3-Cl H  OH      Cl  CH.sub.3                                        OCH.sub.3 H    H  CH.sub.3 CO.sub.2                                                                     Cl  OCH.sub.3                                       OC.sub.2 H.sub.5                                                                        5-F  H  OH      CH.sub.3                                                                          CH.sub.2 OCH.sub.3                              OC.sub.2 H.sub.5                                                                        5-F  H  Et.sub.2 NCO.sub.2                                                                    CH.sub.3                                                                          CH.sub.3                                        OC.sub.2 H.sub.5                                                                        3-Br CH.sub.3                                                                         OH      OCH.sub.3                                                                         OCH.sub.3                                       O .sub.-i-C.sub.3 H.sub.7                                                               H    H  EtOCO.sub.2                                                                           OCH.sub.3                                                                         CH.sub.3                                        O -n-C.sub.3 H.sub.7                                                                    H    H  O -n-C.sub.3 H.sub.7                                                                  CH.sub.3                                                                          OCH.sub.3                                       O -n-C.sub.3 H.sub.7                                                                    6-CH.sub.3                                                                         H  OH      CH.sub.3                                                                          CH.sub.3                                        O .sub.-i-C.sub.4 H.sub.9                                                               3-CF.sub.3                                                                         H  CH.sub.3 OCO.sub.2                                                                    OCH.sub.3                                                                         OCH.sub.3                                       O .sub.-i-C.sub.4 H.sub.9                                                               6-CF.sub.3                                                                         H  OH      OCH.sub.3                                                                         CH.sub.3                                        CO.sub.2 CH.sub.3                                                                       5-CF.sub.3                                                                         H  OH      CH.sub.3                                                                          CH.sub.3                                        CO.sub.2 CH.sub.3                                                                       6-CF.sub.3                                                                         H  OH      CH.sub.3                                                                          OCH.sub.3                                       CO.sub.2 CH.sub.3                                                                       H    H  OH      CH.sub.3 OCO.sub.2                                                                OCH.sub.3                                                                              OC.sub.2 H.sub.5                       SO.sub.2 N(CH.sub.3).sub. 3                                                             6-SCH.sub.3                                                                        H  OH      OCH.sub.3                                                                         OCH.sub.3                                       SO.sub.2 N(CH.sub.3).sub.3                                                              5-SCH.sub.3                                                                        H  CH.sub.3 CO.sub.2                                                                     CH.sub.3                                                                          CH.sub.3                                        SO.sub.2 N(CH.sub.3).sub.3                                                              6-OCH.sub.3                                                                        H  OH      CH.sub.3                                                                          OCH.sub.3                                       SO.sub.2 N(CH.sub.3).sub.3                                                              H    H  (CH.sub.3).sub.2 NCO.sub.2                                                            OCH.sub.3                                                                         OCH.sub.3                                       SO.sub.2 N(CH.sub.3).sub.3                                                              3-OCH.sub.3                                                                        H  OH      OCH.sub.3                                                                         OCH2 CH.sub.3                                   SO.sub.2 N(CH.sub.3).sub.3                                                              H    H  CH.sub.3 NHCO.sub.2                                                                   CH.sub.3                                                                          CH(OCH.sub.2 CH.sub.2 O)                        SO.sub.2 N(CH.sub.2 CH.sub.3).sub.3                                                     3-CH.sub.3                                                                         CH.sub.3                                                                         OH      CH.sub.3                                                                          C.sub.2 H.sub.5                                 SO.sub.2 N(CH.sub.2 CH.sub.3).sub.3                                                     5-CH.sub.3                                                                         H  CF.sub.3 CO.sub.2                                                                     OCH.sub.3                                                                         OC.sub.3 H.sub.5                                SO.sub.2 N(CH.sub.2 CH.sub.3).sub.3                                                     6-Cl H  C.sub.2 H.sub.5 CO.sub.2                                                              OCH.sub.3                                                                         CH.sub.3                                        CO.sub.2 CH.sub.2 CH.sub.3                                                              H    H  C.sub.2 H.sub.5 CO.sub.2                                                              CH.sub.3                                                                          OCH.sub.3                                       CO.sub.2 CH.sub.2 CH.sub.3                                                              H    H  C.sub.2 H.sub.5 CO.sub.2                                                              CH.sub.3                                                                          OCH.sub.3                                       CO.sub.2 CH.sub.3                                                                       H    H  CH.sub.3 OCO.sub.2                                                                    Cl  OCH.sub.3                                       CO.sub.2 CH.sub.3                                                                       5-F  H  OH      CH.sub.3                                                                          CH.sub.2 OCH.sub.3                              CO.sub.2 .sub.-i-C.sub.3 H.sub.7                                                        5-F  H  (C.sub.2 H.sub.5).sub.2 NCO.sub.2                                                     CH.sub.3                                                                          CH.sub.3                                        CO.sub.2 .sub.-i-C.sub.3 H.sub.7                                                        3-Br CH.sub.3                                                                         OH      OCH.sub.3                                                                         OCH.sub.3                                       SO.sub.2 N(OCH.sub.3)CH.sub.3                                                           H    H   -n-C.sub.3 H.sub.7 CO.sub.2                                                          OCH.sub.3                                                                         CH.sub.3                                        CO.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3                                                    H    H  OH      CH.sub.3                                                                          CH.sub.3                                        CO.sub.2 CH.sub.2 CHCH.sub.2                                                            6-CH.sub.3                                                                         H  OH      CH.sub.3                                                                          CH.sub.3                                        CO.sub.2 CH.sub.2 CH.sub.2 Cl                                                           3-CF.sub.3                                                                         h  OH      OCH.sub.3                                                                         OCH.sub.3                                       CO.sub.2 -n-C.sub.4 H.sub.9                                                             6-CF.sub.3                                                                         H  OH      OCH.sub.3                                                                         CH.sub.3                                        SO.sub.2 CH.sub.3                                                                       5-CF.sub.3                                                                         H  OH      CH.sub.3                                                                          CH.sub.3                                        SO.sub.2 CH.sub.3                                                                       3-CF.sub.3                                                                         H  OH      CH.sub.3                                                                          OCH.sub.3                                       SO.sub.2 CH.sub.3                                                                       H    H  CH.sub.3 OCO.sub.2                                                                    OCH.sub.3                                                                         OC.sub.2 H.sub.5                                SO.sub.2 CH.sub.3                                                                       6-SCH.sub.3                                                                        H  OH      OCH.sub.3                                                                         OCH.sub.3                                       SO.sub.2 CH.sub.2 CHCH.sub. 2                                                           5-SCH.sub.3                                                                        H  CH.sub.3 CO.sub.2                                                                     CH.sub.3                                                                          CH.sub.3                                        SO.sub.2 CH.sub.2 CHCH.sub.2                                                            6-OCH.sub.3                                                                        H  OH      CH.sub.3                                                                          OCH.sub.3                                       SO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                     H    H  (CH.sub.3).sub.2 NCO.sub.3                                                            OCH.sub.3                                                                         CH.sub.3                                        SCH.sub.2 CH.sub.3                                                                      3-OCH.sub.3                                                                        H  OH      OCH.sub.3                                                                         OCH.sub.3                                       SCF.sub.3 H    H  CH.sub.3 NHCO.sub.2                                                                   CH.sub.3                                                                          CH(OCH.sub.2 CH.sub.2 O)                        SO.sub.2 CHF.sub.2                                                                      3-CH.sub.3                                                                         CH.sub.3                                                                         OH      CH.sub.3                                                                          C.sub.2 H.sub.5                                 CH.sub.3  5-CH.sub.3                                                                         H  CF.sub.3 CO.sub.2                                                                     OCH.sub.3                                                                         OC.sub.2 H.sub.5                                 .sub.-i-C.sub.3 H.sub.7                                                                6-Cl H  OH      OCH.sub.3                                                                         CH.sub.3                                         -n-C.sub.4 H.sub.9                                                                     H    H  C.sub.2 H.sub.5 CO.sub.2                                                              CH.sub.3                                                                          OCH.sub.3                                       OSO.sub.2 N(CH.sub.3).sub.2                                                             6-Cl H  OH      Cl  CH.sub.3                                        OSO.sub.2 N(CH.sub.3).sub.2                                                             H    H  CH.sub.3 OCO.sub.2                                                                    Cl  OCH.sub.3                                       OSO.sub.2 CH(CH.sub.3).sub.2                                                            5-F  H  CH.sub.3 CO.sub.2                                                                     CH.sub.3                                                                          CH.sub.2 OCH.sub.3                              OSO.sub.2 CH.sub.3                                                                      3-Br CH.sub.3                                                                         OH      OCH.sub.3                                                                         OCH.sub.3                                       OSO.sub.2 CH.sub.3                                                                      H    H   -n-C.sub.3 H.sub.7 OCO.sub.2                                                         OCH.sub.3                                                                         CH.sub.3                                        CH.sub.2 OCH.sub.3                                                                      H    H  C.sub.3 H.sub.7 CO.sub.2                                                              CH.sub.3                                                                          OCH.sub.3                                       CH.sub.2 CH.sub.2 OCH.sub.3                                                             6-CH.sub.3                                                                         H  OH      CH.sub.3                                                                          CH.sub.3                                        OCF.sub.3 3-CF.sub.3                                                                         H  OH      OCH.sub.3                                                                         OCH.sub.3                                       SO.sub.2 .sub.-i-C.sub.3 H.sub.7                                                        5-CF.sub.3                                                                         H  OH      OCH.sub.3                                                                         CH.sub.3                                        CH.sub.2 CH.sub.2 OC.sub.2 H.sub.5                                                      H    H  OH      OCH.sub.3                                                                         OCH.sub.3                                       C.sub.6 H.sub.5                                                                         6-Cl H  OCH.sub.3                                                                             OCH.sub.3                                                                         OCH.sub.3                                       C.sub.6 H.sub.5                                                                         6-Cl H  OCH.sub.3                                                                             OCH.sub.3                                                                         CH.sub.3                                        C.sub.6 H.sub.5                                                                         6-OCH.sub.3                                                                        H  OCH.sub.3                                                                             OCH.sub.3                                                                         CH.sub.3                                        C.sub.6 H.sub.5                                                                         6-OCH.sub.3                                                                        H  OCH.sub.3                                                                             OCH.sub.3                                                                         OCH.sub.3                                       __________________________________________________________________________     *Data refer to molecular ion in electronimpact mass spectrum.            

                                      TABLE 2B                                    __________________________________________________________________________     ##STR38##                                                                    R.sub.5   R.sub.6                                                                            R  R'      X   Y        m.p. (°C.)                      __________________________________________________________________________    Cl        H    H  OH      CH.sub.3                                                                          CH.sub.3                                        Cl        H    H  OH      CH.sub.3                                                                          OCH.sub.3                                       Cl        H    H  OH      OCH.sub.3                                                                         OC.sub.2 H.sub.5                                Cl        H    H  OH      OCH.sub.3                                                                         OCH.sub.3                                                                              137-140°                        F         H    H  OH      CH.sub.3                                                                          CH.sub.3                                        F         H    H  OH      CH.sub.3                                                                          OCH.sub.3                                       Br        H    H  OH      OCH.sub.3                                                                         CH.sub.3                                        Br        H    OH OCH.sub.3                                                                             OCH.sub.3                                           NO.sub.2  H    H  OH      CH.sub.3                                                                          CH(OCH.sub. 2 CH.sub.2 O)                       NO.sub.2  H    CH.sub.3                                                                         OH      CH.sub.3                                                                          C.sub.2 H.sub.5                                 CF.sub.3  H    H  OH      OCH.sub.3                                                                         OC.sub.2 H.sub.5                                CF.sub.3  H    H  OH      OCH.sub.3                                                                         CH.sub.3                                        OCH.sub.3 H    H  OH      CH.sub.3                                                                          OCH.sub.3                                       OCH.sub.3 H    H  OH      CH.sub.3                                                                          CH(OCH.sub.3)                                   OCH.sub.3 H    H  OH      CH.sub.3                                                                          CH.sub.3                                        OCH.sub.3 H    H  OH      OCH.sub.3                                                                         OCH.sub.3                                       OC.sub.2 H.sub.5                                                                        H    H  OH      CH.sub.3                                                                          CH.sub.2 OCH.sub.3                              OC.sub.2 H.sub.5                                                                        H    H  OH      CH.sub.3                                                                          CH.sub.3                                        OC.sub.2 H.sub.5                                                                        H    CH.sub.3                                                                         OH      OCH.sub.3                                                                         OCH.sub.3                                       O .sub.-i-C.sub.3 H.sub.7                                                               H    H  OH      OCH.sub.3                                                                         CH.sub.3                                        O .sub.-i-C.sub.3 H.sub.7                                                               H    H  OH      CH.sub.3                                                                          OCH.sub.3                                       O .sub.-i-C.sub.3 H.sub.7                                                               H    H  OH      CH.sub.3                                                                          CH.sub.3                                        O .sub.-i-C.sub.3 H.sub.7                                                               H    H  OH      OCH.sub.3                                                                         OCH.sub.3                                       O .sub.-i-C.sub.3 H.sub.7                                                               H    H  OH      OCH.sub.3                                                                         CH.sub.3                                        CO.sub.2 CH.sub.3                                                                       H    H  OH      CH.sub.3                                                                          CH.sub.3                                        CO.sub.2 CH.sub.3                                                                       H    H  OH      CH.sub.3                                                                          OCH.sub.3                                       CO.sub.3 CH.sub.3                                                                       H    H  OH      OCH.sub.3                                                                         OC.sub.2 H.sub.5                                SO.sub.2 N(CH.sub.3).sub.2                                                              H    H  OH      OCH.sub.3                                                                         OCH.sub.3                                                                              δ 3.0 and                                                               4.0 (1:1)**                            SO.sub.2 N(CH.sub.3).sub.2                                                              H    H  OH      CH.sub.3                                                                          CH.sub.3 4.O (1:1)*                             SO.sub.2 N(CH.sub.3).sub.2                                                              H    H  OH      H   OCH.sub.3                                       SO.sub.2 N(CH.sub.3).sub.2                                                              H    H  OH      OCH.sub.3                                                                         OCH.sub.3                                       SO.sub.2 N(CH.sub.3).sub.2                                                              H    H  OH      CH.sub.3                                                                          CH(OCH.sub.2 CH.sub.2 O)                        SO.sub.2 N(CH.sub.3).sub.2                                                              H    CH.sub.3                                                                         OH      CH.sub.3                                                                          C.sub.2 H.sub.5                                 SO.sub.2 N(CH.sub.3).sub.2                                                              H    H  OH      OCH.sub.3                                                                         OC.sub.2 H.sub.5                                SO.sub.2 N(CH.sub.3).sub.2                                                              H    H  OH      OCH.sub.3                                                                         CH.sub.3                                        CO.sub.2 CH.sub.2 CH.sub.3                                                              H    H  OH      CH.sub.3                                                                          OCH.sub.3                                       CO.sub.2 CH.sub.2 CH.sub.3                                                              H    H  OH      CH.sub.3                                                                          CH(OCH.sub.3).sub.2                             CO.sub.2 CH.sub.3                                                                       H    H  OH      CH.sub.3                                                                          CH.sub.3                                        CO.sub.2 CH.sub.3                                                                       H    H  OH      CH.sub.3                                                                          OCH.sub.3                                       CO.sub.2 CH.sub.3                                                                       H    H  OH      CH.sub.3                                                                          CH.sub.2 OCH.sub.3                              CO.sub.2 .sub.-i-C.sub.3 H.sub.7                                                        H    H  OH      CH.sub.3                                                                          CH.sub.3                                        CO.sub.2 .sub.-i-C.sub.3 H.sub.7                                                        H    H  OH      OCH.sub.3                                                                         OCH.sub.3                                       SO.sub.2 N(OCH.sub.3)CH.sub.3                                                           H    H  OH      OCH.sub.3                                                                         CH.sub.3                                        CO.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3                                                    H    H  OH      CH.sub.3                                                                          OCH.sub.3                                       CO.sub.2 CH.sub.2 CHCH.sub.2                                                            H    H  OH      CH.sub.3                                                                          CH.sub.3                                        CO.sub.2 CH.sub.2 CH.sub.2 Cl                                                           H    H  OH      OCH.sub.3                                                                         OCH.sub.3                                       CO.sub.2 -n-C.sub.4 H.sub.9                                                             H    H  OH      OCH.sub.3                                                                         OCH.sub.3                                       SO.sub.2 CH.sub.3                                                                       H    H  OH      CH.sub.3                                                                          CH.sub.3                                        SO.sub.2 CH.sub.3                                                                       H    H  OH      CH.sub.3                                                                          OCH.sub.3                                       SO.sub.2 CH.sub.3                                                                       H    H  OH      OCH.sub.3                                                                         OC.sub.2 H.sub.5                                SO.sub.2 CH.sub.3                                                                       H    H  OH      OCH.sub.3                                                                         OCH.sub.3                                       SO.sub.2 CH.sub.2 CHCH.sub.2                                                            H    H  OH      CH.sub.3                                                                          CH.sub.3                                        SO.sub.2 CH.sub.2 CHCH.sub.2                                                            H    H  OH      CH.sub.3                                                                          OCH.sub.3                                       SO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                     H    H  OH      OCH.sub.3                                                                         CH.sub.3                                        SCH.sub.2 CH.sub.3                                                                      H    H  OH      OCH.sub.3                                                                         OCH.sub.3                                       SCF.sub.3 H    H  OH      CH.sub.3                                                                          CH(OCH.sub.2 CH.sub.2 O)                        SO.sub.2 CHF.sub.2                                                                      H    CH.sub.3                                                                         OH      CH.sub.3                                                                          C.sub.2 H.sub.5                                 CH.sub.3  H    H  OH      OCH.sub.3                                                                         OC.sub.2 H.sub.5                                 .sub.-i-C.sub.3 H.sub.7                                                                H    H  OH      OCH.sub.3                                                                         CH.sub.3                                         -n-C.sub.4 H.sub.9                                                                     H    H  OH      CH.sub.3                                                                          OCH.sub.3                                       OSO.sub.2 N(CH.sub.3).sub.2                                                             H    H  OH      CH.sub.3                                                                          CH(OCH.sub.3).sub.2                             OSO.sub.2 N(CH.sub.3).sub.2                                                             H    H  OH      CH.sub.3                                                                          CH.sub.3                                        OSO.sub.2 CH(CH.sub.3).sub.2                                                            H    H  OH      CH.sub.3                                                                          OCH.sub.3                                       OSO.sub.2 C.sub.2 H.sub.5                                                               H    H  OH      CH.sub.3                                                                          CH.sub.2 OCH.sub.3                              OSO.sub.2 CH.sub.3                                                                      H    CH.sub.3                                                                         OH      OCH.sub.3                                                                         OCH.sub.3                                       OSO.sub.2 CH.sub.3                                                                      H    H  OH      OCH.sub.3                                                                         CH.sub.3                                        CH.sub.2 OCH.sub.3                                                                      H    H  OH      CH.sub.3                                                                          OCH.sub.3                                       CH.sub.2 CH.sub.2 OCH.sub.3                                                             H    H  OH      CH.sub.3                                                                          CH.sub.3                                        OCF.sub.3 H    H  OH      OCH.sub.3                                                                         OCH.sub.3                                       SO.sub.2 .sub.-i-C.sub.3 H.sub.7                                                        H    H  OH      OCH.sub.3                                                                         CH.sub.3                                        Cl        3-CF.sub.3                                                                         H  OH      CH.sub.3                                                                          CH.sub.3                                        Cl        5-CF.sub.3                                                                         H  OH      CH.sub.3                                                                          OCH.sub.3                                       Cl        H    H  CH.sub.3 OCO.sub.2                                                                    OCH.sub.3                                                                         OC.sub.2 H.sub.5                                Cl        6-SCH.sub.3                                                                        H  OH      OCH.sub.3                                                                         OCH.sub.3                                       F         5-SCH.sub.3                                                                        H  CH.sub.3 CO.sub.2                                                                     CH.sub.3                                                                          CH.sub.3                                        F         6-OCH.sub.3                                                                        H  OH      CH.sub.3                                                                          OCH.sub.3                                       Br        H    H  (CH.sub.3).sub.2 NCO.sub.2                                                            OCH.sub.3                                                                         CH.sub.3                                        Br        3-OCH.sub.3                                                                        H  OH      OCH.sub.3                                                                         OCH.sub.3                                       NO.sub.2  H    H  CH.sub.3 NHCO.sub.2                                                                   CH.sub.3                                                                          CH(OCH.sub.2 CH.sub.2 O)                        NO.sub.2  3-CH.sub.3                                                                         CH.sub.3                                                                         OH      CH.sub.3                                                                          C.sub.2 H.sub.5                                 CF.sub.3  5-CH.sub.3                                                                         H  CF.sub.3 CO.sub.2                                                                     OCH.sub.3                                                                         OC.sub.2 H.sub.5                                CF.sub.3  6-Cl H  C.sub.2 H.sub.5 CO.sub.2                                                              OCH.sub.3                                                                         CH.sub.3                                        OCH.sub.3 H    H  C.sub.2 H.sub.5 OCO.sub.2                                                             CH.sub.3                                                                          OCH.sub.3                                       OCH.sub.3 5-Cl H  OH      CH.sub.3                                                                          CH(OCH.sub.3).sub.2                             OCH.sub.3 6-Cl H  OH      CH.sub.3                                                                          CH.sub.3                                        OCH.sub.3 H    H   -n-C.sub.3 H.sub.7 CO.sub.2                                                          CH.sub.3                                                                          OCH.sub.3                                       OC.sub.2 H.sub.5                                                                        5-F  H  OH      CH.sub.3                                                                          CH.sub.2 OCH.sub.3                              OC.sub.2 H.sub.5                                                                        5-F  H  Et.sub.2 NCO.sub.2                                                                    CH.sub.3                                                                          CH.sub.3                                        OC.sub.2 H.sub.5                                                                        3-Br CH.sub.3                                                                         OH      OCH.sub.3                                                                         OCH.sub.3                                       O .sub.-i-C.sub.3 H.sub.7                                                               H    H  EtOCO.sub.2                                                                           OCH.sub.3                                                                         CH.sub.3                                        O -n-C.sub.3 H.sub.7                                                                    H    H   -n-C.sub.3 H.sub.7 CO.sub.2                                                          CH.sub.3                                                                          OCH.sub.3                                       O -n-C.sub.3 H.sub.7                                                                    6-CH.sub.3                                                                         H  OH      CH.sub.3                                                                          CH.sub.3                                        O .sub.-i-C.sub.4 H.sub.9                                                               3-CF.sub.3                                                                         H  CH.sub.3 OCO.sub.2                                                                    OCH.sub.3                                                                         OCH.sub.3                                       O .sub.-i-C.sub.4 H.sub.9                                                               5-CF.sub.3                                                                         H  OH      OCH.sub.3                                                                         CH.sub.3                                        CO.sub.2 CH.sub.3                                                                       3-CF.sub.3                                                                         H  OH      CH.sub.3                                                                          CH.sub.3                                        CO.sub.2 CH.sub.3                                                                       5-CF.sub.3                                                                         H  OH      CH.sub.3                                                                          OCH.sub.3                                       CO.sub.2 CH.sub.3                                                                       H    H  CH.sub.3 OCO.sub.2                                                                    OCH.sub.3                                                                         OC.sub.2 H.sub.5                                SO.sub.2 N(CH.sub.3).sub.2                                                              6-SCH.sub.3                                                                        H  OH      OCH.sub.3                                                                         OCH.sub.3                                       SO.sub.2 N(CH.sub.3).sub.2                                                              5-SCH.sub.3                                                                        H  CH.sub.3 CO.sub.2                                                                     CH.sub.3                                                                          CH.sub.3                                        SO.sub.2 N(CH.sub.3).sub.2                                                              6-OCH.sub.3                                                                        H  OH      CH.sub.3                                                                          OCH.sub.3                                       SO.sub.2 N(CH.sub.3).sub.2                                                              H    H  (CH.sub.3).sub.2 NCO.sub.2                                                            OCH.sub.3                                                                         OCH.sub.3                                       SO.sub.2 N(CH.sub.3).sub.2                                                              3-OCH.sub.3                                                                        H  OH      OCH.sub.3                                                                         OCH.sub.2 CH.sub.3                              SO.sub.2 N(CH.sub.3).sub.2                                                              H    H  CH.sub.3 NHCO.sub.2                                                                   CH.sub.3                                                                          CH(OCH.sub.2 CH.sub.2 O)                        SO.sub.2 N(CH.sub.2 CH.sub.3).sub.2                                                     3-CH.sub.3                                                                         CH.sub.3                                                                         OH      CH.sub.3                                                                          C.sub.2 H.sub.5                                 SO.sub.2 N(CH.sub.2 CH.sub.3).sub.2                                                     5-CH.sub.3                                                                         H   -n-C.sub.3 H.sub.7 CO.sub.2                                                          OCH.sub.3                                                                         OC.sub.2 H.sub.5                                SO.sub.2 N(CH.sub.2 CH.sub.3).sub.2                                                     6-Cl H  OH      OCH.sub.3                                                                         CH.sub.3                                        CO.sub.2 CH.sub.2 CH.sub.3                                                              H    H  CF.sub.3 CO.sub.2                                                                     CH.sub.3                                                                          OCH.sub.3                                       CO.sub.2 CH.sub.2 CH.sub.3                                                              5-Cl H  C.sub.2 H.sub.5 OCO.sub.2                                                             CH.sub.3                                                                          CH(OCH.sub.3).sub.2                             CO.sub.2 CH.sub.3                                                                       6-Cl H  OH      CH.sub.3                                                                          CH.sub.3                                        CO.sub.2 CH.sub.3                                                                       H    H  C.sub.2 H.sub.5 CO.sub.2                                                              CH.sub.3                                                                          OCH.sub.3                                       CO.sub.2 CH.sub.3                                                                       5-F  H  OH      CH.sub.3                                                                          CH.sub.2 OCH.sub.3                              CO.sub.2 .sub.-i-C.sub.3 H.sub.7                                                        5-F  H  OH      CH.sub.3                                                                          CH.sub.3                                        CO.sub.2 .sub.-i-C.sub.3 H.sub.7                                                        3-Br CH.sub.3                                                                         OH      OCH.sub.3                                                                         OCH.sub.3                                       SO.sub.2 N(OCH.sub.3)CH.sub.3                                                           H    H  Et.sub.2 NCO.sub.2                                                                    OCH.sub.3                                                                         CH.sub.3                                        CO.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3                                                    H    H   -n-C.sub.3 H.sub.7 OCO.sub.2                                                         CH.sub.3                                                                          OCH.sub.3                                       CO.sub.2 CH.sub.2 CHCH.sub.2                                                            6-CH.sub.3                                                                         H  OH      CH.sub.3                                                                          CH.sub.3                                        CO.sub.2 CH.sub.2 CH.sub.2 Cl                                                           H    H  CH.sub.3 OCO.sub.2                                                                    OCH.sub.3                                                                         OCH.sub.3                                       CO.sub.2 -n-C.sub.4 H.sub.9                                                             H    H  C.sub.2 H.sub.5 CO.sub.2                                                              OCH.sub.3                                                                         CH.sub.3                                        SO.sub.2 CH.sub.3                                                                       3-CF.sub.3                                                                         H  OH      CH.sub.3                                                                          CH.sub.3                                        SO.sub.2 CH.sub.3                                                                       5-CF.sub.3                                                                         H  OH      CH.sub.3                                                                          OCH.sub.3                                       SO.sub.2 CH.sub.3                                                                       H    H  CH.sub.3 OCO.sub.2                                                                    OCH.sub.3                                                                         OC.sub.2 H.sub.5                                SO.sub.2 CH.sub.3                                                                       6-SCH.sub.3                                                                        H  OH      OCH.sub.3                                                                         OCH.sub.3                                       SO.sub.2 CH.sub.2 CHCH.sub.2                                                            5-SCH.sub.3                                                                        H  OH      CH.sub.3                                                                          CH.sub.3                                        SO.sub.2 CH.sub.2 CHCH.sub.2                                                            6-OCH.sub.3                                                                        H  (CH.sub.3).sub.2 NCO.sub.2                                                            CH.sub.3                                                                          OCH.sub.3                                       SO.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                                     H    H  OH      OCH.sub.3                                                                         CH.sub.3                                        SCH.sub.2 CH.sub.3                                                                      3-OCH.sub.3                                                                        H  OH      OCH.sub.3                                                                         OCH.sub.3                                       SCF.sub.3 H    H  CH.sub.3 NHCO.sub.2                                                                   CH.sub.3                                                                          CH(OCH.sub.2 CH.sub.2 O)                        SO.sub.2 CHF.sub.2                                                                      3-CH.sub.3                                                                         CH.sub.3                                                                         OH      CH.sub.3                                                                          C.sub.2 H.sub.5                                 CH.sub.3  5-CH.sub.3                                                                         H  C.sub.2 H.sub.5 OCO.sub.2                                                             OCH.sub.3                                                                         OC.sub.2 H.sub.5                                 .sub.-i-C.sub.3 H.sub.7                                                                6-Cl H  OH      OCH.sub.3                                                                         CH.sub.3                                         -n-C.sub.4 H.sub.9                                                                     H    H   -n-C.sub.3 H.sub.7 OCO.sub.2                                                         CH.sub.3                                                                          OCH.sub.3                                       OSO.sub.2 N(CH.sub.3).sub.2                                                             6-Cl H  C.sub.2 H.sub.5 CO.sub.2                                                              CH.sub.3                                                                          CH.sub.3                                        OSO.sub.2 N(CH.sub.3).sub.2                                                             H    H   -n-C.sub.3 H.sub.7 CO.sub.2                                                          CH.sub.3                                                                          OCH.sub. 3                                      OSO.sub.2 CH(CH.sub.3).sub.2                                                            5-F  H  OH      CH.sub.3                                                                          CH.sub.2 OCH.sub.3                              OSO.sub.2 CH.sub.3                                                                      3-Br CH.sub.3                                                                         C.sub.2 H.sub.5 NHCO.sub.2                                                            OCH.sub.3                                                                         OCH.sub.3                                       OSO.sub.2 CH.sub.3                                                                      H    H  (C.sub.2 H.sub.5).sub.2 NCO.sub.2                                                     OCH.sub.3                                                                         CH.sub.3                                        CH.sub.2 OCH.sub.3                                                                      H    H  CH.sub.3 CO.sub.2                                                                     CH.sub.3                                                                          OCH.sub.3                                       CH.sub.2 CH.sub.2 OCH.sub.3                                                             6-CH.sub.3                                                                         H  OH      CH.sub.3                                                                          CH.sub.3                                        OCF.sub.3 H    H  C.sub.2 H.sub.5 OCO.sub.2                                                             OCH.sub.3                                                                         OCH.sub.3                                       SO.sub.2 .sub.-i-C.sub.3 H.sub.7                                                        H    H   -n-C.sub.3 H.sub.7 NHCO.sub.2                                                        OCH.sub.3                                                                         CH.sub.3                                        CH.sub.2 CH.sub.2 OC.sub.2 H.sub.5                                                      H    H  OH      OCH.sub.3                                                                         CH.sub.3                                        C.sub.6 H.sub.5                                                                         6-Cl H  OCH.sub.3                                                                             OCH.sub.3                                                                         OCH.sub.3                                       C.sub.6 H.sub.5                                                                         6-Cl H  OCH.sub.3                                                                             OCH.sub.3                                                                         CH.sub.3                                        C.sub.6 H.sub.5                                                                         6-OCH.sub.3                                                                        H  OCH.sub.3                                                                             OCH.sub.3                                                                         OCH.sub.3                                       C.sub.6 H.sub.5                                                                         6-OCH.sub.3                                                                        H  OCH.sub.3                                                                             OCH.sub.3                                                                         CH.sub.3                                        __________________________________________________________________________     **Data refer to characteristic signals in NMR spectrum (CDCl.sub.3) in pp     downfield form tetramethylsilane.                                        

                                      TABLE 2c                                    __________________________________________________________________________     ##STR39##                                                                                                                    m.p.                          R'      R   R.sub.5     R.sub.6                                                                            X    Y          Z  (°C.)                  __________________________________________________________________________    OH      H   OCH.sub.2 CH.sub.2 OCH.sub.3                                                              H    CH.sub.3                                                                           H          CH                               OH      H   OCH.sub.2 CHCH.sub.2                                                                      H    CH.sub.3                                                                           CH.sub.3   N                                OH      H   OCH.sub.2 CHCH                                                                            6-OCH.sub.3                                                                        CH.sub.3                                                                           CH.sub.3   CH                               OH      H   C.sub.6 H.sub.5                                                                           H    CH.sub.3                                                                           CH.sub.3   N                                OH      H   N N         H    CH.sub.3                                                                           OCH.sub.3  CH                                           O CH.sub.3                                                        OH      H   N N         H    OCH.sub.3                                                                          OCH.sub.3  N                                            O                                                                 OH      H   Cl          H    OCH.sub.3                                                                          OCH.sub.2 CCH                                                                            N                                CONHCH.sub.3                                                                          H   Cl          H    OCH.sub.3                                                                          OCH.sub.2 CF.sub.3                                                                       CH                               OH      H   Cl          H    OCH.sub.3                                                                          OCH.sub.2 CH.sub.2 OCH.sub.3                                                             N                                OH      H   Cl          H    OCH.sub.3                                                                          CH.sub.2 SCH.sub.3                                                                       CH                               OH      H   F           H    OCH.sub.3                                                                          OCF.sub.2 H                                                                              CH                               OH      H   F           H    OCH.sub.3                                                                          SCF.sub.2 H                                                                              CH                               OH      H   F           3-OCF.sub.2 H                                                                      OCH.sub.3                                                                          C(CH.sub.3)(OCH.sub.3).sub.2                                                             CH                               OH      H   F           H    OCH.sub.3                                                                          CF.sub.3   N                                OH      H   Br          H    OCH.sub.3                                                                          N(CH.sub.3).sub.2                                                                        CH                               OH      CH.sub.3                                                                          Br          H    OCH.sub.3                                                                          C(CH.sub.3)(SCH.sub.3).sub.2                                                             N                                OH      CH.sub.3                                                                          Br          H    OCF.sub.2 H                                                                        CH(SCH.sub.2 CH.sub.2 S)                                                                 CH                               OH      CH.sub.3                                                                          Br          H    CF.sub.3                                                                           CH.sub.2 CH.sub.3                                                                        CH                               OH      CH.sub.3                                                                          Br          H    F    OCH.sub.3  CH                               OH      CH.sub.3                                                                          Br          H    OC.sub.2 H.sub.5                                                                   C(CH.sub.3)(OCH.sub.2 CH.sub.2 O)                                                        CH                               OH      H                                                                                  ##STR40##  H    CH.sub.3                                                                           H          CH                               OH      H                                                                                  ##STR41##  H    CH.sub.3                                                                           CH.sub.3   CH                               OH      H                                                                                  ##STR42##  H    CH.sub.3                                                                           OCH.sub.3  CH                               COCF.sub.3                                                                            H   O .sub.-n-C.sub.3 H.sub.7                                                                 H    OCH.sub.3                                                                          OCH.sub.3  CH                               OH      H   O .sub.-n-C.sub.3 H.sub.7                                                                 H    OCH.sub.3                                                                          OCH.sub.2 CHCH.sub.2                                                                     CH                               OH      H   O .sub.-n-C.sub.3 H.sub.7                                                                 H    OCH.sub.3                                                                          OCH.sub.2 CCH                                                                            N                                OH      H   OCH.sub.3   5-Br OCH.sub.3                                                                          OCH.sub.2 CF.sub.3                                                                       N                                OH      H   OCH.sub.3   H    OCH.sub.3                                                                          OCH.sub.2 CH.sub.2 OCH.sub.3                                                             N                                OH      H   OCH.sub.3   H    OCH.sub.3                                                                          CH.sub.2 SCH.sub.3                                                                       CH                               OH      H   NO.sub.2    H    OCH.sub.3                                                                          OCF.sub.2 H                                                                              CH                               OH      H   NO.sub.2    H    OCH.sub.3                                                                          SCF.sub.2 H                                                                              CH                               OH      H   NO.sub.2    H    OCH.sub.3                                                                          C(CH.sub.3)(OCH.sub.3).sub.2                                                             CH                               OH      H   CF.sub.3    H    OCH.sub.3                                                                          CF.sub.3   CH                               OH      H   CF.sub.3    H    OCH.sub.3                                                                          N(CH.sub.3).sub.2                                                                        CH                               OH      CH.sub.3                                                                          CF.sub.3    H    OCH.sub.3                                                                          C(CH.sub.3)(SCH.sub.3).sub.2                                                             CH                               OH      CH.sub.3                                                                          CO.sub.2 CH.sub.3                                                                         H    OCF.sub.2 H                                                                        CH(SCH.sub.2 CH.sub.2 S)                                                                 CH                               OH      CH.sub.3                                                                          CO.sub.2 CH.sub.3                                                                         H    CF.sub.3                                                                           CH.sub.2 CH.sub.3                                                                        CH                               OH      CH.sub.3                                                                          CO.sub.2 CH.sub.3                                                                         H    F    OCH.sub.3  CH                               OH      CH.sub.3                                                                          CO.sub.2 CH.sub.3                                                                         H    OC.sub.2 H.sub.5                                                                   C(CH.sub.3)(OCH.sub.2 CH.sub.2 O)                                                        CH                               OH      H                                                                                  ##STR43##  H    CH.sub.3                                                                           H          N                                OH      H                                                                                  ##STR44##  H    CH.sub.3                                                                           CH.sub.3   N                                OH      H                                                                                  ##STR45##  H    CH.sub.3                                                                           OCH.sub.3  CH                               OH      H   CO.sub.2 CH.sub.2 CHCH.sub.2                                                              H    OCH.sub.3                                                                          OCH.sub.3  CH                               OH      H   CO.sub.2 CH.sub.2 CHCH.sub.2                                                              H    OCH.sub.3                                                                          OCH.sub.2 CHCH.sub.2                                                                     CH                               OH      H   CO.sub.2 CH.sub.2 CHCH.sub.2                                                              H    OCH.sub.3                                                                          OCH.sub.2 CCH                                                                            N                                OH      H   SO.sub.2 N(CH.sub.3).sub.2                                                                H    OCH.sub.3                                                                          OCH.sub.2 CF.sub.3                                                                       N                                OH      H   SO.sub.2 N(CH.sub.3).sub.2                                                                H    OCH.sub.3                                                                          OCH.sub.2 CH.sub.2 OCH.sub.3                                                             N                                OH      H   SO.sub.2 N(CH.sub.3).sub.2                                                                H    OCH.sub.3                                                                          CH.sub.2 SCH.sub.3                                                                       N                                OH      H   SO.sub.2 N(OCH.sub.3)CH.sub.3                                                             H    OCH.sub.3                                                                          OCF.sub.2 H                                                                              CH                               OH      H   SO.sub.2 N(CH.sub.3)C.sub.2 H.sub.5                                                       H    OCH.sub.3                                                                          SCF.sub.2 H                                                                              CH                               OH      H   SCF.sub.3   H    OCH.sub.3                                                                          C(CH.sub.3)(OCH.sub.3).sub.2                                                             CH                               OH      H   SO.sub.2 CHF.sub.2                                                                        H    OCH.sub.3                                                                          CF.sub.3   CH                               OH      H   CO.sub.2 CH.sub.2 CH.sub.2 Cl                                                             H    OCH.sub.3                                                                          N(CH.sub.3).sub.2                                                                        CH                               OH      CH.sub.3                                                                          CO.sub.2 CH.sub.2 CH.sub.3                                                                H    OCH.sub.3                                                                          C(CH.sub.3)(SCH.sub.3).sub.2                                                             CH                               OH      H   CO.sub.2 CH.sub.2 CH.sub.3                                                                H    OCF.sub.2 H                                                                        CH(SCH.sub.2 CH.sub.2 S)                                                                 CH                               OH      H   CO.sub. 2 CH.sub.2 CH.sub.3                                                               H    CF.sub.3                                                                           CH.sub.2 CH.sub.3                                                                        CH                               OH      H   SO.sub.2 CH.sub.3                                                                         H    F    OCH.sub.3  CH                               OCO .sub.-i-C.sub.3 H.sub.7                                                           H   SO.sub.2 CH.sub.3                                                                         H    OC.sub.2 H.sub.5                                                                   C(CH.sub.3)(OCH.sub.2 CH.sub.2 O)                                                        CH                               OH      H                                                                                  ##STR46##  H    CH.sub.3                                                                           H          N                                OH      H                                                                                  ##STR47##  H    CH.sub.3                                                                           CH.sub.3   N                                OH      H                                                                                  ##STR48##  6-OCF.sub.2 H                                                                      CH.sub.3                                                                           OCH.sub.3  CH                               OH      H                                                                                  ##STR49##  H    OCH.sub.3                                                                          OCH.sub.3  CH                               OH      H   OCH.sub.3   H    OCH.sub.3                                                                          OCH.sub.2 CCH                                                                            CH                               OH      H   OCH.sub.3   H    OCH.sub.3                                                                          OCH.sub.2 CF.sub.3                                                                       CH                               OH      H   OCH.sub.3   H    OCH.sub.3                                                                          OCH.sub.2 CH.sub.2 OCH.sub.3                                                             CH                               OH      H   OC.sub.2 H.sub.5                                                                          H    OCH.sub.3                                                                          CH.sub.2 SCH.sub.3                                                                       CH                               OH      H   OC.sub.2 H.sub.5                                                                          3-F  OCH.sub.3                                                                          OCF.sub.2 H                                                                              CH                               OCO.sub.2 CH.sub.2 CH.sub.3                                                           H   OC.sub.2 H.sub.5                                                                          H    OCH.sub.3                                                                          SCF.sub.2 H                                                                              CH                               OH      H   CH.sub.3    H    OCH.sub.3                                                                          C(CH.sub.3)(OCH.sub.3).sub.2                                                             N                                OH      H   CH.sub.3    H    OCH.sub.3                                                                          CF.sub.3   N                                OH      H   CH.sub.3    H    OCH.sub.3                                                                          N(CH.sub.3).sub.2                                                                        N                                OH      CH.sub.3                                                                           .sub.-i-C.sub.3 H.sub.7                                                                  H    OCH.sub.3                                                                          C(CH.sub.3)(SCH.sub.3).sub.2                                                             CH                               OH      H    .sub.-i-C.sub.3 H.sub.7                                                                  H    OCF.sub.2 H                                                                        CH(SCH.sub.2 CH.sub.2 S)                                                                 CH                               OH      H    .sub.-i-C.sub.3 H.sub.7                                                                  H    CF.sub.3                                                                           CH.sub.2 CH.sub.3                                                                        CH                               OH      H    .sub.-i-C.sub.3 H.sub.7                                                                  H    F    OCH.sub.3  CH                               OH      H    .sub.-n-C.sub.4 H.sub.9                                                                  H    OC.sub.2 H.sub.5                                                                   C(CH.sub.3)(OCH.sub.2 CH.sub.2 O)                                                        N                                __________________________________________________________________________

                                      TABLE 3                                     __________________________________________________________________________     ##STR50##                                                                    R.sub.7                                                                              R  R'      X     Y        Z  m.p. (°C.)                         __________________________________________________________________________    OH     H  OH      CH.sub.3                                                                            CH.sub.3 CH                                           CH.sub.3                                                                             H  OCON(CH.sub.3).sub.2                                                                  OCH.sub.3                                                                           CH.sub.3 N                                            OCH.sub.3                                                                            H  OH      Cl    CH.sub.3 CH                                           F      H  OH      CH.sub.3                                                                            CH.sub.3 CH                                           Cl     H  OH      OCH.sub.3                                                                           OCH.sub.3                                                                              CH                                           Br     H  OH      F     OCH.sub.3                                                                              CH                                           SO.sub.2 N(CH.sub.3).sub.2                                                           H  OH      CH.sub.3                                                                            OCH.sub.3                                                                              CH                                           OSO.sub.2 CH.sub.3                                                                   H  OH      OCF.sub.2 H                                                                         OCH.sub.3                                                                              CH                                           SO.sub.2 CH.sub.3                                                                    H  OH      CH.sub.2 F                                                                          OC.sub.2 H.sub.5                                                                       CH                                           OH     CH.sub.3                                                                         OH      OCH.sub.2 CH.sub.3                                                                  CH.sub.2 OCH.sub.3                                                                     N                                            CH.sub.3                                                                             H  OH      CF.sub.3                                                                            N(CH.sub.3).sub.2                                                                      CH                                           OCH.sub.3                                                                            H  OH      OCH.sub.3                                                                           CF.sub.3 CH                                           F      H  OCO.sub.2 CH.sub.2 CH.sub.3                                                           CH.sub.3                                                                            CH(OCH.sub.3).sub.2                                                                    CH                                           Cl     H  OH      OCH.sub.3                                                                           OCF.sub.2 H                                                                            N                                            Br     H  OH      OCH.sub.3                                                                           OCH.sub.2 CH.sub.2 OCH.sub.3                                                           N                                            SO.sub.2 N(CH.sub.3).sub.2                                                           H  OH      OCH.sub.3                                                                           CH.sub.2 SCH.sub.3                                                                     N                                            OSO.sub.2 CH.sub.3                                                                   H  OH      OCH.sub.3                                                                           OCH.sub.2 CCH                                                                          CH                                           SCH.sub.3 SCH.sub.3                                                                  H H                                                                              OH OH   OCH.sub.2 CH.sub.3 CH.sub.3                                                          ##STR51##                                                                             CH CH                                        CH.sub.3                                                                             H  OH      CH.sub.3                                                                            OCH.sub.3                                                                              N                                            OH     H  OH      CH.sub.3                                                                            OCH.sub.3                                                                              N                                            __________________________________________________________________________

                                      TABLE 4                                     __________________________________________________________________________     ##STR52##                                                                                                          m.p.                                    R.sub.8  R  R'      X     Y        Z  (°C.)                            __________________________________________________________________________    CH.sub.3 H  OCON(CH.sub.3).sub.2                                                                  OCH.sub.3                                                                            ##STR53##                                                                             N                                          CH.sub.2 CH.sub.3                                                                      H  OH      Cl    OCH.sub.3                                                                              CH                                         OCH.sub.3                                                                              H  OH      CH.sub.3                                                                            CH.sub.2 OC.sub.2 H.sub.5                                                              CH                                         OCH.sub.2 CH.sub.3                                                                     H  OH      OCH.sub.3                                                                           CH.sub.3 CH                                         F        H  OH      F     CH.sub.3 CH                                         Cl       H  OH      CH.sub.3                                                                            CH.sub.3 CH                                         Br       H  OH      OCF.sub.2 H                                                                         CH.sub.3 CH                                         SO.sub.2 N(CH.sub.2 CH.sub.3).sub. 2                                                   H  OH      CH.sub.2 F                                                                          OCH.sub.3                                                                              CH                                         SO.sub.2 N(CH.sub.3).sub.2                                                             CH.sub.3                                                                         OH      OCH.sub.2 CH.sub.3                                                                  OCH.sub.3                                                                              N                                          SO.sub.2 N(OCH.sub.3)CH.sub.3                                                          H  OH      CF.sub.3                                                                            OCH.sub.3                                                                              CH                                         SCH.sub.2 CHCH.sub.2                                                                   H  OH      OCH.sub.3                                                                           OCH.sub.3                                                                              CH                                         SO.sub.2 C.sub.2 H.sub.5                                                               H  OCO.sub.2 CH.sub.2 CH.sub.3                                                           CH.sub.3                                                                            OCH.sub.3                                                                              CH                                         S .sub.-n-C.sub.3 H.sub.7                                                              H  OH      OCH.sub.3                                                                           C.sub.2 H.sub.5                                                                        N                                          SO.sub.2 CH.sub.3                                                                      H  OH      OCH.sub.3                                                                           OC.sub.2 H.sub.5                                                                       N                                          SCH.sub.3                                                                              H  OH      OCH.sub.3                                                                           SCF.sub.2 H                                                                            N                                          CH.sub.3 H  OH      OCH.sub.3                                                                           C(CH.sub.3)(SCH.sub.3).sub.2                                                           CH                                         F        H  OH      OCH.sub.2 CH.sub.3                                                                  OCF.sub.2 H                                                                            CH                                         Cl       H  OH      CH.sub.3                                                                            CH(OC.sub.2 H.sub.5).sub.2                                                             CH                                         Br       H  OH      CH.sub.3                                                                            CH.sub.3 N                                          OCH.sub.3                                                                              H  OH      CH.sub.3                                                                            CH.sub.3 N                                          __________________________________________________________________________

                                      TABLE 5                                     __________________________________________________________________________     ##STR54##                                                                                                           m.p.                                   L  R.sub.9  R  R'      X     Y      Z  (°C.)                           __________________________________________________________________________    L.sub.4                                                                          CH.sub.3 H  OH      CH.sub.3                                                                            OCH.sub.3                                                                            CH                                        L.sub.4                                                                          F        H  OCON(CH.sub.3).sub.2                                                                  OCH.sub.3                                                                           OCH.sub.3                                                                            N                                         L.sub.4                                                                          NO.sub.2 H  OH      Cl    OCH.sub.3                                                                            CH                                        L.sub.4                                                                          CO.sub.2 C.sub.2 H.sub.5                                                               H  OH      CH.sub.3                                                                            OCH.sub.3                                                                            CH                                        L.sub.4                                                                          SO.sub.2 N(CH.sub.3).sub.2                                                             H  OH      OCH.sub.3                                                                           CH.sub.2 SCH.sub.3                                                                   CH                                        L.sub.4                                                                          S .sub.-i-C.sub.3 H.sub.7                                                              H  OH      F     CH.sub.3                                                                             CH                                        L.sub.5                                                                           .sub.-n-C.sub.3 H.sub.7                                                               H  OH      CH.sub.3                                                                            N(CH.sub.3).sub.2                                                                    CH                                        L.sub.5                                                                          Cl       H  OH      OCF.sub. 2 H                                                                        CH.sub.2 OCH.sub.3                                                                   CH                                        L.sub.5                                                                          Br       H  OH      CH.sub.2 F                                                                          CH.sub.2 OCH.sub.3                                                                   CH                                        L.sub.5                                                                          CO.sub.2 CH.sub.3                                                                      CH.sub.3                                                                         OH      OCH.sub.2 CH.sub.3                                                                  CH.sub.2 OCH.sub.3                                                                   N                                         L.sub.5                                                                          SO.sub.2 N(C.sub.2 H.sub.5).sub.2                                                      H  OH      CF.sub.3                                                                            CH.sub.3                                                                             CH                                        L.sub.5                                                                          SO.sub.2 N(OCH.sub.3)CH.sub.3                                                          H  OH      OCH.sub.3                                                                           CH.sub.3                                                                             CH                                        L.sub.5                                                                          SO.sub.2 C.sub.2 H.sub.5                                                               H  OCO.sub.2 CH.sub.2 CH.sub.3                                                           CH.sub.3                                                                            CH.sub.3                                                                             CH                                        L.sub.5                                                                          SCH.sub.2 CHCH.sub.2                                                                   H  OH      OCH.sub.3                                                                           CH.sub.3                                                                             N                                         L.sub.5                                                                          SO.sub.2 CH.sub.3                                                                      H  OH      OCH.sub.3                                                                            ##STR55##                                                                           N                                         L.sub.6                                                                          F        H  OH      OCH.sub.3                                                                           CH(OCH.sub.3).sub.2                                                                  CH                                        L.sub.6                                                                          CO.sub.2 .sub.-i-C.sub.3 H.sub.7                                                       H  OH      OCH.sub.2 CH.sub.3                                                                  OCH.sub.3                                                                            CH                                        L.sub.6                                                                          SO.sub.2 CH.sub.3                                                                      H  OH      CH.sub.3                                                                            OCH.sub.3                                                                            CH                                        L.sub.6                                                                          SO.sub.2 N(CH.sub.3).sub.2                                                             H  OH      CH.sub.3                                                                            OCH.sub.3                                                                            N                                         L.sub.6                                                                          Br       H  OH      CH.sub.3                                                                            OCH.sub.3                                                                            N                                         __________________________________________________________________________

                                      TABLE 6                                     __________________________________________________________________________     ##STR56##                                                                                                        m.p.                                      R.sub.10                                                                             R   R'      X      Y     Z   (°C.)                              __________________________________________________________________________    Cl     H   OH      CH.sub.3                                                                             CH.sub.3                                                                            CH                                            NO.sub.2                                                                             H   OCON(CH.sub.3).sub.2                                                                  OCH.sub.3                                                                            CH.sub.3                                                                            N                                             CO.sub.2 CH.sub.3                                                                    H   OH      Cl     CH.sub.3                                                                            CH                                            CO.sub.2 CH.sub.2 CH.sub.3                                                           H   OH      CH.sub.3                                                                             CH.sub.3                                                                            CH                                            SO.sub.2 N(CH.sub.3).sub.2                                                           H   OH      OCH.sub.3                                                                            CH.sub.3                                                                            CH                                            OSO.sub.2 CH.sub.3                                                                   H   OH      F      OCH.sub.3                                                                           CH                                            SO.sub.2 CH.sub.3                                                                    H   OH      CH.sub.3                                                                             OCH.sub.3                                                                           CH                                            SO.sub.2 CH.sub.2 CH.sub.3                                                           H   OH      OCF.sub.2 H                                                                          OCH.sub.3                                                                           CH                                            OCH.sub.3                                                                            H   OH      CH.sub.2 F                                                                           OCH.sub.3                                                                           CH                                            OCH.sub.2 CH.sub.3                                                                   CH.sub.3                                                                          OH      OCH.sub.2 CH.sub.3                                                                   OCH.sub.3                                                                           N                                             OCH.sub.2 CH.sub.3                                                                   H   OH      CF.sub.3                                                                             CH.sub.2 SCH.sub.3                                                                  CH                                            OCH.sub.2 CH.sub.3                                                                   H   OH      OCH.sub.3                                                                            CF.sub.3                                                                            CH                                            OCH.sub.3                                                                            H   OCO.sub.2 CH.sub.2 CH.sub.3                                                           CH.sub.3                                                                             CH.sub.2 CH.sub.3                                                                   CH                                            SO.sub.2 CH.sub.2 CH.sub.3                                                           H   OH      OCH.sub.3                                                                            OCH.sub.3                                                                           N                                             SO.sub.2 CH.sub.3                                                                    H   OH      OCH.sub.3                                                                            SCF.sub.2 H                                                                         N                                             OSO.sub.2 CH.sub.3                                                                   H   OH      OCH.sub.3                                                                            CH.sub.3                                                                            N                                             CO.sub.2 CH.sub.2 CH.sub.3                                                           H   OH      OCH.sub.3                                                                            CH.sub.3                                                                            CH                                            CO.sub.2 CH.sub.3                                                                    H   OH      OCH.sub.2 CH.sub.3                                                                   CH.sub.3                                                                            CH                                            CO.sub.2 CH.sub.3                                                                    H   OH      CH.sub.3                                                                             CH.sub.3                                                                            CH                                            CO.sub.2 CH.sub.3                                                                    H   OH      CH.sub.3                                                                             OCH.sub.3                                                                           N                                             NO.sub.2                                                                             H   OH      CH.sub.3                                                                             OCH.sub.3                                                                           N                                             __________________________________________________________________________

                                      TABLE 7                                     __________________________________________________________________________     ##STR57##                                                                                                                  m.p.                            Q.sub.1                                                                           R.sub.11                                                                           R.sub.12                                                                           R.sub.13                                                                         R  R'      X     Y        Z  (°C.)                    __________________________________________________________________________    O   H    H    H  H  OH      CH.sub.3                                                                            OCH.sub.3                                                                              CH                                 S   H    H    H  H  OCON(CH.sub.3).sub.2                                                                  OCH.sub.3                                                                           OCH.sub.3                                                                              N                                  SO.sub.2                                                                          H    H    H  H  OH      Cl    OCH.sub.3                                                                              CH                                 NH  H    H    H  H  OH      CH.sub.3                                                                            OCH.sub.3                                                                              CH                                 NCH.sub.3                                                                         H    H    H  H  OH      OCH.sub.3                                                                           CH.sub.3 CH                                 O   CH.sub.3                                                                           CH.sub.3                                                                           H  H  OH      F     CH.sub.3 CH                                 S   CH.sub.3                                                                           CH.sub.3                                                                           H  H  OH      CH.sub.3                                                                            CH.sub.3 CH                                 SO.sub.2                                                                          CH.sub.3                                                                           CH.sub.3                                                                           H  H  OH      OCF.sub.2 H                                                                         CH.sub.3 CH                                 NH  CH.sub.3                                                                           CH.sub.3                                                                           H  H  OH      CH.sub.2 F                                                                          OCH.sub.2 CH.sub.3                                                                     CH                                 NCH.sub.3                                                                         CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                         CH.sub.3                                                                         OH      OCH.sub.2 CH.sub.3                                                                  OCH.sub.2 CH.sub.3                                                                     N                                  O   CH.sub.2 CH.sub.3                                                                  CH.sub.3                                                                           H  H  OH      CF.sub.3                                                                            OCH.sub.2 CH.sub.3                                                                     CH                                 S   CH.sub.2 CH.sub.3                                                                  CH.sub.3                                                                           H  H  OH      OCH.sub.3                                                                           CF.sub.3 CH                                 SO.sub.2                                                                          CH.sub.2 CH.sub.3                                                                  CH.sub.2 CH.sub.3                                                                  H  H  OCO.sub.2 CH.sub.2 CH.sub.3                                                           CH.sub.3                                                                            OCF.sub.2 H                                                                            CH                                 NH  CH.sub.2 CH.sub.3                                                                  CH.sub.3                                                                           H  H  OH      OCH.sub.3                                                                           OCH.sub.3                                                                              N                                  NCH.sub.3                                                                         CH.sub.2 CH.sub.3                                                                  CH.sub.3                                                                           H  H  OH      OCH.sub.3                                                                           OCH.sub.3                                                                              N                                  O   H    CH.sub.3                                                                           H  H  OH      OCH.sub.3                                                                           OCH.sub.3                                                                              N                                  S   H    CH.sub.3                                                                           H  H  OH      OCH.sub.3                                                                           OCH.sub.3                                                                              CH                                 SO.sub.2                                                                          H    CH.sub.3                                                                           H  H  OH      OCH.sub.2 CH.sub.3                                                                  OCH.sub.3                                                                              CH                                 NH  H    CH.sub.3                                                                           H  H  OH      CH.sub.3                                                                            C(CH.sub.3)(OCH.sub.3).sub.2                                                           CH                                 NCH.sub.3                                                                         H    CH.sub.3                                                                           H  H  OH      CH.sub.3                                                                            CH.sub.3 N                                  O   CH.sub.3                                                                           CH.sub.3                                                                           H  H  OH      CH.sub.3                                                                            CH.sub.3 N                                  __________________________________________________________________________

                                      TABLE 8                                     __________________________________________________________________________     ##STR58##                                                                                                         m.p.                                     Q.sub.2                                                                           R.sub.14                                                                         R.sub.15                                                                         R  R'      X     Y      Z  (°C.)                             __________________________________________________________________________    O   H  H  H  OH      CH.sub.3                                                                            CH.sub.3                                                                             CH                                          O   H  CH.sub.3                                                                         H  OCON(CH.sub.3).sub.2                                                                  OCH.sub.3                                                                           CH.sub.3                                                                             N                                           O   H  H  H  OH      Cl    CH.sub.3                                                                             CH                                          O   H  CH.sub.3                                                                         H  OH      CH.sub.3                                                                            CH.sub.3                                                                             CH                                          O   CH.sub.3                                                                         H  H  OH      OCH.sub.3                                                                           CH(OCH.sub.3).sub.2                                                                  CH                                          O   CH.sub.3                                                                         CH.sub.3                                                                         H  OH      F     OCH.sub.3                                                                            CH                                          O   CH.sub.3                                                                         H  H  OH      CH.sub.3                                                                            OCH.sub.3                                                                            CH                                          S   H  CH.sub.3                                                                         H  OH      OCF.sub.2 H                                                                         OCH.sub.3                                                                            CH                                          S   H  H  H  OH      CH.sub.2 F                                                                          OCH.sub.3                                                                            CH                                          S   H  CH.sub.3                                                                         CH.sub.3                                                                         OH      OCH.sub.2 CH.sub.3                                                                  CH.sub.2 SCH.sub.3                                                                   N                                           S   H  H  H  OH      CF.sub.3                                                                            OCH.sub.2 CH.sub.3                                                                   CH                                          S   CH.sub.3                                                                         CH.sub.3                                                                         H  OH      OCH.sub.3                                                                           OCH.sub.3                                                                            CH                                          S   CH.sub.3                                                                         H  H  OCO.sub.2 CH.sub.2 CH.sub.3                                                           CH.sub.3                                                                            OCH.sub.3                                                                            CH                                          S   CH.sub.3                                                                         CH.sub.3                                                                         H  OH      OCH.sub.3                                                                           OCH.sub.3                                                                            N                                           NH  H  H  H  OH      OCH.sub.3                                                                           OCH.sub.3                                                                            N                                           NH  CH.sub.3                                                                         CH.sub.3                                                                         H  OH      OCH.sub.3                                                                           OCH.sub.3                                                                            N                                           NH  H  H  H  OH      OCH.sub.3                                                                           OCH.sub.3                                                                            CH                                          NCH.sub.3                                                                         H  CH.sub.3                                                                         H  OH      OCH.sub.2 CH.sub.3                                                                  CH.sub.3                                                                             CH                                          NCH.sub.3                                                                         CH.sub.3                                                                         H  H  OH      CH.sub.3                                                                            CH.sub.3                                                                             CH                                          NCH.sub.3                                                                         CH.sub.3                                                                         CH.sub.3                                                                         H  OH      CH.sub.3                                                                            CH.sub.3                                                                             N                                           NCH.sub.3                                                                         CH.sub.3                                                                         H  H  OH      CH.sub.3                                                                            CH.sub.3                                                                             N                                           __________________________________________________________________________

                                      TABLE 9                                     __________________________________________________________________________     ##STR59##                                                                                                          m.p.                                    L  m R.sub.13                                                                         R.sub.16                                                                         R  R'      X     Y      Z  (°C.)                            __________________________________________________________________________    L-10                                                                             0 H  CH.sub.3                                                                         H  OH      CH.sub.3                                                                            CH.sub.3                                                                             CH                                         L-10                                                                             1 H  CH.sub.3                                                                         H  OCON(CH.sub.3).sub.2                                                                  OCH.sub.3                                                                           CH.sub.3                                                                             N                                          L-10                                                                             0 H  CH.sub.3                                                                         H  OH      Cl    CH.sub.3                                                                             CH                                         L-11                                                                             0 CH.sub.3                                                                         -- H  OH      CH.sub.3                                                                            CH.sub.3                                                                             CH                                         L-11                                                                             0 CH.sub.3                                                                         -- H  OH      OCH.sub.3                                                                           CH(OCH.sub.3).sub.2                                                                  CH                                         L-11                                                                             0 CH.sub.3                                                                         -- H  OH      F     OCH.sub.3                                                                            CH                                         L-11                                                                             0 H  -- H  OH      CH.sub.3                                                                            OCH.sub.3                                                                            CH                                         L-12                                                                             1 H  -- H  OH      OCF.sub.2 H                                                                         OCH.sub.3                                                                            CH                                         L-12                                                                             0 H  -- H  OH      CH.sub.2 F                                                                          OCH.sub.3                                                                            CH                                         L-12                                                                             1 H  -- CH.sub.3                                                                         OH      OCH.sub.2 CH.sub.3                                                                  CH.sub.2 SCH.sub.3                                                                   N                                          L-13                                                                             0 CH.sub.3                                                                         -- H  OH      CF.sub.3                                                                            OCH.sub.2 CH.sub.3                                                                   CH                                         L-13                                                                             1 H  -- H  OH      OCH.sub.3                                                                           OCH.sub.3                                                                            CH                                         L-13                                                                             0 H  -- H  OCO.sub.2 CH.sub.2 CH.sub.3                                                           CH.sub.3                                                                            OCH.sub.3                                                                            CH                                         L-13                                                                             1 H  -- H  OH      OCH.sub.3                                                                           OCH.sub.3                                                                            N                                          L-14                                                                             0 H  -- H  OH      OCH.sub.3                                                                           OCH.sub.3                                                                            N                                          L-14                                                                             1 H  -- H  OH      OCH.sub.3                                                                           OCH.sub.3                                                                            N                                          L-14                                                                             0 CH.sub.3                                                                         -- H  OH      OCH.sub.3                                                                           OCH.sub.3                                                                            CH                                         L-10                                                                             1 H  CH.sub.3                                                                         H  OH      OCH.sub.2 CH.sub.3                                                                  CH.sub.3                                                                             CH                                         L-10                                                                             0 H  C.sub.2 H.sub.5                                                                  H  OH      CH.sub.3                                                                            CH.sub.3                                                                             CH                                         L-10                                                                             1 H  C.sub.2 H.sub.5                                                                  H  OH      CH.sub.3                                                                            CH.sub.3                                                                             N                                          L-10                                                                             0 H  C.sub.2 H.sub.5                                                                  H  OH      CH.sub.3                                                                            CH.sub.3                                                                             N                                          __________________________________________________________________________

                                      TABLE 10                                    __________________________________________________________________________     ##STR60##                                                                                                        m.p.                                      L  R.sub.17                                                                          R.sub.18                                                                         R  R'      X     Y     Z  (°C.)                              __________________________________________________________________________    L.sub.15                                                                         H   -- H  OH      CH.sub.3                                                                            CH.sub.3                                                                            CH                                           L.sub.15                                                                         H   -- H  OCON(CH.sub.3).sub.2                                                                  OCH.sub.3                                                                           CH.sub.3                                                                            N                                            L.sub.15                                                                         H   -- H  OH      C1    CH.sub.3                                                                            CH                                           L.sub.15                                                                         H   -- H  OH      CH.sub.3                                                                            CH.sub.3                                                                            CH                                           L.sub.15                                                                         H   -- H  OH      OCH.sub.3                                                                           CH(OCH.sub.3).sub.2                                                                 CH                                           L.sub.15                                                                         H   -- H  OH      F     OCH.sub.3                                                                           CH                                           L.sub.15                                                                         H   -- H  OH      CH.sub.3                                                                            OCH.sub.3                                                                           CH                                           L.sub.15                                                                         CH.sub.3                                                                          -- H  OH      OCF.sub.2 H                                                                         OCH.sub.3                                                                           CH                                           L.sub.15                                                                         CH.sub.3                                                                          -- H  OH      CH.sub.2 F                                                                          OCH.sub.3                                                                           CH                                           L.sub.15                                                                         CH.sub.3                                                                          -- CH.sub.3                                                                         OH      OCH.sub.2 CH.sub.3                                                                  CH.sub.2 SCH.sub.3                                                                  N                                            L.sub.16                                                                         CH.sub.3                                                                          -- H  OH      CF.sub.3                                                                            OCH.sub.2 CH.sub.3                                                                  CH                                           L.sub.16                                                                         CH.sub.3                                                                          -- H  OH      OCH.sub.3                                                                           OCH.sub.3                                                                           CH                                           L.sub.16                                                                         CH.sub.3                                                                          -- H  OCO.sub.2 CH.sub.2 CH.sub.3                                                           CH.sub.3                                                                            OCH.sub.3                                                                           CH                                           L.sub.16                                                                         CH.sub.3                                                                          -- H  OH      OCH.sub.3                                                                           OCH.sub.3                                                                           N                                            L.sub.16                                                                         H   -- H  OH      OCH.sub.3                                                                           OCH.sub.3                                                                           N                                            L.sub.16                                                                         H   -- H  OH      OCH.sub.3                                                                           OCH.sub.3                                                                           N                                            L.sub.16                                                                         H   -- H  OH      OCH.sub.3                                                                           OCH.sub.3                                                                           CH                                           L.sub.17                                                                         CH.sub.3                                                                          CH.sub.3                                                                         H  OH      OCH.sub.2 CH.sub.3                                                                  CH.sub.3                                                                            CH                                           L.sub.17                                                                         CH.sub.3                                                                          H  H  OH      CH.sub.3                                                                            CH.sub.3                                                                            CH                                           L.sub.17                                                                         CH.sub.3                                                                          CH.sub.3                                                                         H  OH      CH.sub.3                                                                            CH.sub.3                                                                            N                                            L.sub.17                                                                         CH.sub.3                                                                          CH.sub.3                                                                         H  OH      CH.sub.3                                                                            CH.sub.3                                                                            N                                            __________________________________________________________________________

                  TABLE 11                                                        ______________________________________                                         ##STR61##                                                                    R.sub.5   R.sub.6 R      R'      A                                            ______________________________________                                        CH.sub.3  H       H      OH      A.sub.2 : Y.sub.1 = CH.sub.2 ;                                                X.sub.1 = CH.sub.3                            .sub.-i-C.sub.3 H.sub.7                                                                H       H      OH      A.sub.2 : Y.sub.1 = O;                                                        X.sub.1 = OCH.sub.3                          OC.sub.2 H.sub.5                                                                        H       H      OH      A.sub.2 : Y.sub.1 = CH.sub.2 ;                                                X.sub.1 = OCF.sub.2 H                        O -n-C.sub.4 H.sub.9                                                                    H       H      OH      A.sub.3 : X.sub.1 = CH.sub.3                 F         3-CF.sub.3                                                                            H      OCO.sub.2 CH.sub.3                                                                    A.sub.3 : X.sub.1 = OCH.sub.2 CH.sub.3       C1        H       H      OCO.sub.2 CH.sub.3                                                                    A.sub. 4 : X.sub.1 = OCH.sub.3 ;                                              Y.sub.2 = H                                  NO.sub.2  H       CH.sub.3                                                                             OCO.sub.2 CH.sub.3                                                                    A.sub.4 : X.sub.1 = CH.sub.3 ;                                                Y.sub.2 = CH.sub.3                           CF.sub.3  H       H      OCO.sub.2 CH.sub.3                                                                    A.sub.5 : X.sub.2 = CH.sub.3 ;                                                Y.sub.3 = OCH.sub.3                          CO.sub.2 CH.sub.3                                                                       H       H      OCO.sub.2 CH.sub.3                                                                    A.sub.5 : X.sub.2 = CH.sub.3 ;                                                Y.sub.3 = SCH.sub.3                          CO.sub.2 CH.sub.2 CH.sub.3                                                              3-CH.sub.3                                                                            H      OCO.sub.2 CH.sub.3                                                                    A.sub.5 : X.sub.2 = CH.sub.3 ;                                                Y.sub.3 = C.sub.2 H.sub.5                    SO.sub.2 N(CH.sub.3).sub.2                                                              H       H      OCO.sub.2 CH.sub.3                                                                    A.sub.6 : X.sub.3 = CH.sub.3                 SO.sub.2 N(C.sub.2 H.sub.5).sub.2                                                       H       H      OCO.sub.2 CH.sub.3                                                                    A.sub.6 : X.sub.3 = OCH.sub.3                OSO.sub.2 CH.sub.2 CH.sub.3                                                             H       CH.sub.3                                                                             OCO.sub.2 CH.sub.3                                                                    A.sub.2 : Y.sub.1 = O;                                                        X.sub.1 = OCH.sub.2 CH.sub.3                 SCH.sub.3 6-Cl    H      OCO.sub.2 CH.sub.3                                                                    A.sub.2 : Y.sub.1 = CH.sub.2 ;                                                X.sub.1 = OCH.sub.3                          SO.sub.2 CF.sub.3                                                                       H       H      OH      A.sub.2 : Y.sub.1 = O;                                                        X.sub.1 = CH.sub.3                           OCHF.sub.2                                                                              H       H      OCOCH.sub.3                                                                           A.sub.3 : X.sub.1 = OCF.sub.2 H              OCH.sub.2 CHCH.sub.2                                                                    H       H      OH      A.sub.3 : X.sub.1 = OCH.sub.3                C.sub.6 H.sub.5                                                                         H       H      OH      A.sub.4 : X.sub.1 = OCH.sub.3 ;                                               Y.sub.2 = CH.sub.3                            ##STR62##                                                                              H       H      OH      A.sub.4 : X.sub.1 = OCF.sub.2 H; Y.sub.2                                      = H                                           ##STR63##                                                                              H       H      OH      A.sub.5 : X.sub.2 = CH.sub.2 CF.sub.3 ;                                       Y.sub.3 = CH.sub.3                           CH.sub.2 OCH.sub.3                                                                      H       H      OH      A.sub.6 : X.sub.3 = OCH.sub.3                CH.sub.2 OCH.sub.3                                                                      H       H      OH      A.sub.6 : X.sub.3 = CH.sub.3                 ______________________________________                                    

                  TABLE 12                                                        ______________________________________                                         ##STR64##                                                                    L             R      R'        A                                              ______________________________________                                        L-2: R.sub.7 = SO.sub.2 N(CH.sub.3).sub.2                                                   H      OH        A.sub.2 : Y.sub.1 = CH.sub.2 ;                                                X.sub.1 = CH.sub.3                             L-2: R.sub.7 = OSO.sub.2 CH.sub.3                                                           H      OH        A.sub.2 : Y.sub.1 = O;                                                        X.sub.1 = OCH.sub.3                            L-2: R.sub.7 = Cl                                                                           H      OH        A.sub.2 : Y.sub.1 = CH.sub.2 ;                                                X.sub.1 = OCF.sub.2 H                          L-2: R.sub.7 = Br                                                                           H      OH        A.sub.3 : X.sub.1 = CH.sub.3                   L-3: R.sub.8 = CH.sub.3                                                                     H      OCO.sub.2 CH.sub.3                                                                      A.sub.3 : X.sub.1 = OCH.sub.2 CH.sub.3         L-3: R.sub.8 = OCH.sub.3                                                                    H      OCO.sub.2 CH.sub.3                                                                      A.sub.4 : X.sub.1 =  OCH.sub.3 ;                                              Y.sub.2 = H                                    L-3: R.sub.8 = SO.sub.2 CH.sub.2 CH.sub.3                                                   CH.sub.3                                                                             OCO.sub.2 CH.sub.3                                                                      A.sub.4 : X.sub.1 = CH.sub.3 ;                                                Y.sub.2 = CH.sub.3                             L-4: R.sub.9 = CO.sub.2 CH.sub.3                                                            H      OCO.sub.2 CH.sub.3                                                                      A.sub.5 : X.sub.2 = CH.sub.3 ;                                                Y.sub.3 = OCH.sub.3                            L-5: R.sub.9 = CO.sub.2 - .sub.-i-C.sub.3 H.sub.7                                           H      OCO.sub.2 CH.sub.3                                                                      A.sub.5 : X.sub.2 = CH.sub.3 ;                                                Y.sub.3 = SCH.sub.3                            L-6: R.sub.9 = Cl                                                                           H      OCO.sub.2 CH.sub.3                                                                      A.sub.5 : X.sub.2 = CH.sub.3 ;                                                Y.sub.3 = C.sub.2 H.sub.5                      L-4: R.sub.9 = NO.sub.2                                                                     H      OCO.sub.2 CH.sub.3                                                                      A.sub.6 : X.sub.3 = CH.sub.3                   L-5: R.sub.9 = SO.sub.2 N(CH.sub.3).sub. 2                                                  H      OCO.sub.2 CH.sub.3                                                                      A.sub.6 : X.sub.3 = OCH.sub.3                  L-6: R.sub.9 = C.sub.2 H.sub.5                                                              CH.sub.3                                                                             OCO.sub.2 CH.sub.3                                                                      A.sub.2 : Y.sub.1 = O;                                                        X.sub.1 = OCH.sub.2 CH.sub.3                   L-7: R.sub.10 = CO.sub.2 CH.sub.3                                                           H      OCO.sub.2 CH.sub.3                                                                      A.sub.2 : Y.sub.1 = CH.sub.2;                                                 X.sub.1 = OCH.sub.3                            L-7: R.sub.10 = SO.sub.2 N(CH.sub.3).sub.2                                                  H      OH        A.sub.2 : Y.sub.1 = O;                                                        X.sub.1 = CH.sub.3                             L-7: R.sub.10 = OSO.sub.2 CH.sub.3                                                          H      OCOCH.sub.3                                                                             A.sub.3 : X.sub.1 = OCF.sub.2 H                L-8:          H      OH        A.sub.3 : X.sub.1 = OCH.sub.3                  R.sub.11 = R.sub.12 = R.sub.13 = CH.sub.3 ;                                   m = 0; Q.sub.1 = S                                                            L-9: R.sub.14 = CH.sub.3 ;                                                                  H      OH        A.sub.4 : X.sub.1 = OCH.sub.3 ;                R.sub.15 = H;                  Y.sub.2 = CH.sub.3                             Q.sub.2 = NCH.sub.3                                                           L-10: R.sub.16 = C.sub.2 H.sub.5 ;                                                          H      OH        A.sub.4 : X.sub.1 = OCF.sub.2 H;               R.sub.13 = H; M = 1            Y.sub.2 = H                                    L-11: R.sub.13 = H; m = 0                                                                   H      OH        A.sub.5 : X.sub.2 = C.sub.2 H.sub.5 ;                                         Y.sub.3 = OC.sub.2 H.sub.5                     L-12: R.sub.13 = CH.sub.3 ; m = 0                                                           H      OH        A.sub.5 : X.sub.2 = CH.sub.2 CF.sub.3 ;                                       Y.sub.3 = CH.sub.3                             L-13: R.sub.13 = CH.sub.3 ; m = 0                                                           H      OH        A.sub.5 : X.sub.2 = CH.sub.3 ;                                                Y.sub.3 = C.sub.2 H.sub.5                      L-14: R.sub.16 = CH.sub.3                                                                   H      OH        A.sub.6 : X.sub.3 =OCH.sub.3                   L-15: R.sub.17 = H                                                                          H      OH        A.sub.2 : Y.sub.1 = CH.sub.2 ;                                                X.sub.1 = CH.sub.3                             L-15: R.sub.17 = H                                                                          H      OH        A.sub.2 : Y.sub.1 = O;                                                        X.sub.1 = OCH.sub.3                            L-15: R.sub.17 = H                                                                          H      OH        A.sub.2 : Y.sub.1 = CH.sub.2 ;                                                X.sub.1 = OCF.sub.2 H                          L-16: R.sub.17 = CH.sub.3                                                                   H      OH        A.sub.3 : X.sub.1 = CH.sub.3                   L-16: R.sub.17 = CH.sub.3                                                                   H      OCO.sub.2 CH.sub.3                                                                      A.sub.3 : X.sub.1 = OCH.sub.2 CH.sub.3         L-16: R.sub.17 = CH.sub.3                                                                   H      OCO.sub.2 CH.sub.3                                                                      A.sub.4 : X.sub.1 = OCH.sub.3 ;                                               Y.sub.2 = H                                    L-17: R.sub.17 = H;                                                                         CH.sub.3                                                                             OCO.sub.2 CH.sub.3                                                                      A.sub.4 : X.sub.1 = CH.sub.3 ;                 R.sub.18 = CH.sub.3            Y.sub.2 = CH.sub.3                             L-17: R.sub.17 = H;                                                                         H      OCO.sub.2 CH.sub.3                                                                      A.sub.5 : X.sub.2 = CH.sub.3 ;                 R.sub.18 = CH.sub.3            Y.sub.3 = OCH.sub.3                            L-17: R.sub.17 = H;                                                                         H      OCO.sub.2 CH.sub.3                                                                      A.sub.5 : X.sub.2 = CH.sub.3 ;                 R.sub.18 = CH.sub.3            Y.sub.3 = SCH.sub.3                            L-8: R.sub.11 = R.sub.12 =                                                                  H      OCO.sub.2 CH.sub.3                                                                      A.sub.5 : X.sub.2 = CH.sub.3 ;                 R.sub.13 = 1; H;               Y.sub.3 = C.sub.2 H.sub.5                      m = 1; Q.sub.1 = SO.sub.2                                                     L-8: R.sub.11 = R.sub.12 =                                                                  H      OCO.sub.2 CH.sub.3                                                                      A.sub.6 : X.sub.3 = CH.sub.3                   R.sub.13 = H;                                                                 m = 1; Q.sub.1 = SO.sub.2                                                     L-8: R.sub.11 = R.sub.12 =                                                                  H      OCO.sub.2 CH.sub.3                                                                      A.sub.6 : X.sub.3 = OCH.sub.3                  R.sub.13 = H;                                                                 m =  1; Q.sub.1 = SO.sub.2                                                    L-9: R.sub.14 = R.sub.15 = H;                                                               CH.sub.3                                                                             OCO.sub.2 CH.sub.3                                                                      A.sub.2 : Y.sub.1 = O;                         Q.sub.2 = S                    X.sub.1 = OCH.sub.2 CH.sub.3                   L-9: R.sub.14 = R.sub.15 = H;                                                               H      OCO.sub.2 CH.sub.3                                                                      A.sub.2 : Y.sub.1 = CH.sub.2 ;                 Q.sub.2 = S                    X.sub.1 = OCH.sub.3                            L-9: R.sub.14 = R.sub.15 = H;                                                               H      OH        A.sub.2 : Y.sub.1 = O;                         Q.sub.2 = S                    X.sub.1 = CH.sub.3                             L-10: R.sub.13 = R.sub.16 = CH.sub.3 ;                                                      H      OCOCH.sub.3                                                                             A.sub.3 : X.sub.1 = OCF.sub.2 H                m = 0                                                                         L-10: R.sub.13 = R.sub.16 = CH.sub.3 ;                                                      H      OH        A.sub.3 : X.sub.1 = OCH.sub.3                  m = 0                                                                         L-10: R.sub.13 = R.sub.16 = CH.sub.3 ;                                                      H      OH        A.sub.4 : X.sub.1 =  OCH.sub.3 ;               m = 0                          Y.sub.2 = CH.sub.3                             L-11: R.sub.13 = CH.sub.3 ; m = 0                                                           H      OH        A.sub.4 : X.sub.1 = OCF.sub.2 H;                                              Y.sub.2 = H                                    L-11: R.sub.13 = CH.sub.3 ; m = 0                                                           H      OH        A.sub.5 : X.sub.2 = C.sub.2 H.sub.5 ;                                         Y.sub.3 = OC.sub.2 H.sub.5                     L-11: R.sub.13 = CH.sub.3 ; m = 0                                                           H      OH        A.sub.5 : X.sub.2 = CH.sub.2 CF.sub.3 ;                                       Y.sub.3 = CH.sub.3                             L-12: R.sub.13 = H; m = 1                                                                   H      OH        A.sub.5 : X.sub.2 = CH.sub.3 ;                                                Y.sub.3 = C.sub.2 H.sub.5                      L-13: R.sub.13 = H; m = 1                                                                   H      OH        A.sub.6 : X.sub.3 = OCH.sub.3                  L-14: R.sub.16 = H                                                                          H      OH        A.sub.6 : X.sub.3 = CH.sub.3                   ______________________________________                                    

Formulations

Useful formulations of the compounds of Formula I can be prepared inconventional ways. They include dusts, granules, pellets, solutions,suspensions, emulsions, wettable powders, emulsifiable concentrates andthe like. Many of these may be applied directly. Sprayable formulationscan be extended in suitable media and used at spray volumes of from afew liters to several hundred liters per hectare. High strengthcompositions are primarily used as intermediates for furtherformulation. The formulations, broadly, contain about 0.1% to 99% byweight of active ingredient(s) and at least one of (a) about 0.1% to 20%surfactant(s) and (b) about 1% to 99.9% solid or liquid diluent(s). Morespecifically, they will contain these ingredients in the followingapproximate proportions:

                  TABLE 13                                                        ______________________________________                                                    Active  Weight Percent*                                                       Ingredient                                                                            Diluent(s)                                                                              Surfactant(s)                                   ______________________________________                                        Wettable Powders                                                                            20-90      0-74     1-10                                        Oil Suspensions,                                                                             3-50     40-95     0-15                                        Emulsion, Solutions,                                                          (including Emulsifiable                                                       Concentrates)                                                                 Aqueous Suspension                                                                          10-50     40-84     1-20                                        Dusts          1-25     70-99     0-5                                         Granules and Pellets                                                                        0.1-95      5-99.9  0-15                                        High Strength 90-99      0-10     0-2                                         Compositions                                                                  ______________________________________                                         *Active ingredient plus at least one of a Surfactant or a Diluent equals      100 weight percent.                                                      

Lower or higher levels of active ingredient can, of course, be presentdepending on the intended use and the physical properties of thecompound. Higher ratios of surfactant to active ingredient are sometimesdesirable, and are achieved by incorporation into the formulation or bytank mixing.

Typical solid diluents are described in Watkins, et al., "Handbook ofInsecticide Dust Diluents and Carriers", 2nd Ed., Dorland Books,Caldwell, N.J., but other solids, either mined or manufactured, may beused. The more absorptive diluents are preferred for wettable powdersand the denser ones for dusts. Typical liquid diluents and solvents aredescribed in Marsden, "Solvents Guide," 2nd Ed., Interscience, N.Y.,1950. Solubility under 0.1% is preferred for suspension concentrates;solution concentrates are preferably stable against phase separation at0° C. "McCutcheon's Detergents and Emulsifiers Annual", MC PublishingCorp., Ridgewood, N.J., as well as Sisely and Wood, "Encyclopedia ofSurface Active Agents", Chemical Publishing Co., Inc., N.Y., 1964, listsurfactants and recommended uses. All formulations can contain minoramounts of additives to reduce foaming, caking, corrosion,microbiological growth, etc.

The methods of making such compositions are well known. Solutions areprepared by simply mixing the ingredients. Fine solid compositions aremade by blending and, usually, grinding as in a hammer or fluid energymill. Suspensions are prepared by wet milling (see, for example,Littler, U.S. Pat. No. 3,060,084). Granules and pellets may be made byspraying the active material upon preformed granular carriers or byagglomeration techniques. See J. E. Browning, "Agglomeration", ChemicalEngineering, Dec. 4, 1967, pp. 147ff. and "Perry's Chemical Engineer'sHandbook", 5th Ed., McGraw-Hill, N.Y., 1973, pp. 8-57ff.

For further information regarding the art of formulation, see forexample:

H. M. Loux, U.S. Pat. No. 3,235,361, Feb. 15, 1966, Col. 6, line 16through Col. 7, line 19 and Examples 10 through 41;

R. W. Luckenbaugh, U.S. Pat. No. 3,309,192, Mar. 14, 1967, Col. 5, line43 through Col. 7, line 62 and Examples 8, 12, 15, 39, 41, 52, 53, 58,132, 138-140, 162-164, 166, 167 and 169-182;

H. Gysin and E. Knusli, U.S. Pat. No. 2,891,855, Jun. 23, 1959, Col. 3,line 66 through Col. 5, line 17 and Examples 1-4;

G. C. Klingman, "Weed Control as a Science", John Wiley and Sons, Inc.,N.Y., 1961, pp. 81-96; and

J. D. Fryer and S. A. Evans, "Weed Control Handbook", 5th Ed., BlackwellScientific Publications, Oxford, 1968, pp. 101-103.

In the following examples, all parts are by weight unless otherwiseindicated.

EXAMPLE 7

Wettable Powder

    ______________________________________                                        2-[[1-(4,6-dimethylpyrimidin-2-yl)amino]-1-(hydroxy-                                                       80%                                              imino)methyl]aminosulfonyl]benzoic acid, methyl                               ester                                                                         sodium alkylnaphthalenesulfonate                                                                           2%                                               sodium ligninsulfonate       2%                                               synthetic amorphous silica   3%                                               kaolinite                    13%                                              ______________________________________                                    

The ingredients are blended, hammer-milled until all the solids areessentially under 50 microns, reblended, and packaged.

EXAMPLE 8

Wettable Powder

    ______________________________________                                        2-[[1-(4-methoxy-6-methylpyrimidin-2-yl)amino]-1-                                                          50%                                              (hydroxyimino)methyl]aminosulfonyl]benzoic acid,                              methyl ester                                                                  sodium alkylnaphthalenesulfonate                                                                           2%                                               low viscosity methyl cellulose                                                                             2%                                               diatomaceous earth           46%                                              ______________________________________                                    

The ingredients are blended, coarsely hammer-milled and then air-milledto produce particles essentially all below 10 microns in diameter. Theproduct is reblended before packaging.

EXAMPLE 9

Granule

    ______________________________________                                        Wettable Powder of Example 8                                                                            5%                                                  attapulgite granules      95%                                                 (U.S.S. 20-40 mesh; 0.84-0.42 mm)                                             ______________________________________                                    

A slurry of wettable powder containing ≈25% solids is sprayed on thesurface of attapulgite granules in a double-cone blender. The granulesare dried and packaged.

EXAMPLE 10

Extruded Pellet

    ______________________________________                                        N',N'--dimethyl-N--[[1-(4,6-dimethyl-1,3,5-triazin-2-yl)-                                                  25%                                              amino]-1-(hydroxyimino)methyl]-1,2-benzenedisulfon-                           amide                                                                         anhydrous sodium sulfate     10%                                              crude calcium ligninsulfonate                                                                              5%                                               sodium alkylnaphthalenesulfonate                                                                           1%                                               calcium/magnesium bentonite  59%                                              ______________________________________                                    

The ingredients are blended, hammer-milled and then moistened with about12% water. The mixture is extruded as cylinders about 3 mm diameterwhich are cut to produce pellets about 3 mm long. These may be useddirectly after drying, or the dried pellets may be crushed to pass aU.S.S. No. 20 sieve (0.84 mm openings). The granules held on a U.S.S.No. 40 sieve (0.42 mm openings) may be packaged for use and the finesrecycled.

EXAMPLE 11

Oil Suspension

    ______________________________________                                        N',N' --dimethyl-N--[[1-(4-methoxy-6-methylpyrimidin-2-                                                    25%                                              yl)amino]-1-(hydroxyimino)methyl]-1,2-benzenedi-                              sulfonamide                                                                   polyoxyethylene sorbitol hexaoleate                                                                        5%                                               highly aliphatic hydrocarbon oil                                                                           70%                                              ______________________________________                                    

The ingredients are ground together in a sand mill until the solidparticles have been reduced to under about 5 microns. The resultingthick suspension may be applied directly, but preferably after beingextended with oils or emulsified in water.

EXAMPLE 12

Wettable Powder

    ______________________________________                                        2-[[1-(4,6-dimethylpyrimidin-2-yl)amino]-1-(hydroxy-                                                       20%                                              imino)methyl]aminosulfonyl]benzoic acid, methyl                               ester                                                                         sodium alkylnaphthalenesulfonate                                                                           4%                                               sodium ligninsulfonate       4%                                               low viscosity methyl cellulose                                                                             3%                                               attapulgite                  69%                                              ______________________________________                                    

The ingredients are thoroughly blended. After grinding in a hammer-millto produce particles essentially all below 100 microns, the material isreblended and sifted through a U.S.S. No. 50 sieve (0.3 mm opening) andpackaged.

EXAMPLE 13

Low Strength Granule

    ______________________________________                                        N',N'--dimethyl-N--[[1-(4,6-dimethyl-1,3,5-triazin-2-yl)-                                                  1%                                               animo]-1-(hydroxyimino)methyl]-1,2-benzenedisulfon-                           amide                                                                         N,N--dimethylformamide       9%                                               attapulgit granules          90%                                              (U.S.S. 20-40 sieve)                                                          ______________________________________                                    

The active ingredient is dissolved in the solvent and the solution issprayed upon dedusted granules in a double cone blender. After sprayingof the solution has been completed, the blender is allowed to run for ashort period and then the granules are packaged.

EXAMPLE 14

Aqueous Suspension

    ______________________________________                                        N',N'--dimethyl-N--[[1-(4-methoxy-6-methylpyrimidin-2-                                                     40%                                              yl)amino]-1-(hydroxyimino)methyl]-1,2-benzenedi-                              sulfonamide                                                                   polyacrylic acid thickener   0.3%                                             dodecylphenol polyethylene glycol ether                                                                    0.5%                                             disodium phosphate           1%                                               monosodium phosphate         0.5%                                             polyvinyl alcohol            1.0%                                             water                        56.7%                                            ______________________________________                                    

The ingredients are blended and ground together in a sand mill toproduce particles essentially all under 5 microns in size.

EXAMPLE 15

Solution

    ______________________________________                                        2-[[1-(4-methoxy-6-methylpyrimidin-2-yl)amino]-1-                                                          5%                                               (hydroxyimino)methyl]aminosulfonyl]benzoic acid,                              methyl ester                                                                  water                        95%                                              ______________________________________                                    

The salt is added directly to the water with stirring to produce thesolution, which may then be packaged for use.

EXAMPLE 16

Low Strength Granule

    ______________________________________                                        2-[[1-(4,6-dimethylpyrimidin-2-yl)amino]-1-(hydroxy-                                                      0.1%                                              imino)methyl]aminosulfonyl]benzoic acid, methyl                               ester                                                                         attapulgite granules        99.9%                                             (U.S.S. 20-40 mesh)                                                           ______________________________________                                    

The active ingredient is dissolved in a solvent and the solution issprayed upon dedusted granules in a double-cone blender. After sprayingof the solution has been completed, the material is warmed to evaporatethe solvent. The material is allowed to cool and then packaged.

EXAMPLE 17

Granule

    ______________________________________                                        2-[[1-(4-methoxy-6-methylpyrimidin-2-yl)amino]-1-                                                          80%                                              (hydroxyimino)methyl]aminosulfonyl]benzoic acid                               methyl ester                                                                  wetting agent                1%                                               crude ligninsulfonate salt (containing                                                                     10%                                              5-20% of the natural sugars)                                                  attapulgite clay             9%                                               ______________________________________                                    

The ingredients are blended and milled to pass through a 100 meshscreen. This material is then added to a fluid bed granulator, the airflow is adjusted to gently fluidize the material, and a fine spray ofwater is sprayed onto the fluidized material. The fluidization andspraying are continued until granules of the desired size range aremade. The spraying is stopped, but fluidization is continued, optionallywith heat, until the water content is reduced to the desired level,generally less than 1%. The material is then discharged, screened to thedesired size range, generally 14-100 mesh (1410-1490microns), andpackaged for use.

EXAMPLE 18

High Strength Concentrate

    ______________________________________                                        N',N'--dimethyl-N--[[1-(4-methoxy-6-methylpyrimidin-2-                                                     99%                                              yl)amino]-1-(hydroxyimino)methyl]-1,2-benzenedi-                              sulfonamide                                                                   silica aerogel               0.5%                                             synthetic amorphous silica   0.5%                                             ______________________________________                                    

The ingredients are blended and ground in a hammer-mill to produce amaterial essentially all passing a U.S.S. No. 50 screen (0.3 mmopening). The concentrate may be formulated further if necessary.

EXAMPLE 19

Wettable Powder

    ______________________________________                                        N',N'--dimethyl-N--[[1-(4,6-dimethyl-1,3,5-triazin-2-yl)-                                                  90%                                              amino]-1-(hydroxyimino)methyl]-1,2-benzenedisulfon-                           amide                                                                         dioctyl sodium sulfosuccinate                                                                              0.1%                                             synthetic fine silica        9.9%                                             ______________________________________                                    

The ingredients are blended and ground in a hammer-mill to produceparticles essentially all below 100 microns. The material is siftedthrough a U.S.S. No. 50 screen and then packaged.

EXAMPLE 20

Wettable Powder

    ______________________________________                                        2-[[1-(4,6-dimethylpyrimidin-2-yl)amino]-1-(hydroxy-                                                       40%                                              imino)methyl]aminosulfonyl]benzoic acid, methyl                               ester                                                                         sodium ligninsulfonate       20%                                              montmorillonite clay         40%                                              ______________________________________                                    

The ingredients are thoroughly blended, coarsely hammer-milled and thenair-milled to produce particles essentially all below 10 microns insize. The material is reblended and then packaged.

EXAMPLE 21

Oil Suspension

    ______________________________________                                        N',N'--dimethyl-N--[[1-(dimethyl-1,3,5-triazin-2-yl)-                                                      35%                                              amino]-1-(hydroxyimino)methyl]-1,2-benzenedisulfon-                           amide                                                                         blend of polyalcohol carboxylic                                                                            6%                                               esters and oil soluble petroleum                                              sulfonates                                                                    xylene                       59%                                              ______________________________________                                    

The ingredients are combined and ground together in a sand mill toproduce particles essentially all below 5 microns. The product can beused directly, extended with oils, or emulsified in water.

EXAMPLE 22

Dust

    ______________________________________                                        2-[[1-(4-methoxy-6-methylpyrimidin-2-yl)amino]-1-                                                          10%                                              (hydroxyimino)methyl]aminosulfonyl]benzoic acid                               methyl ester                                                                  attapulgite                  10%                                              Pyrophyllite                 80%                                              ______________________________________                                    

The active ingredient is blended with attapulgite and then passedthrough a hammer-mill to produce particles substantially all below 200microns. The ground concentrate is then blended with powderedpyrophyllite until homogeneous.

EXAMPLE 23

Emulsifiable Concentrate

    ______________________________________                                        N',N'--dimethyl-N--[[1-(4-methoxy-6-methylpyrimidin-2-                                                     20%                                              yl)amino]-1-(hydroxyimino)methyl]-1,2-benzenedi-                              sulfonamide                                                                   chlorobenzene                74%                                              sorbitan monostearate and polyoxyethylene                                     condensates thereof          6%                                               ______________________________________                                    

The ingredients are combined and stirred to produce a solution which canbe emulsified in water for application.

Utility

The compounds of the present invention are active herbicides. They haveutility for broad-spectrum pre-and/or post-emergence weed control inareas where complete control of all vegetation is desired, such asaround fuel storage tanks, ammunition depots, industrial storage areas,parking lots, drivein theaters, around billboards, highway and railroadstructures. Alternatively, the subject compounds are useful for theselective pre- or post-emergence weed control in crops, such as wheatand barley.

The rates of application for the compounds of the invention aredetermined by a number of factors, including their use as selective orgeneral herbicides, the crop species involved, the types of weeds to becontrolled, weather and climate, formulations selected, mode ofapplication, amount of foliage present, etc. In general terms, thesubject compounds should be applied at levels of around 0.03 to 5 kg/ha,the lower rates being suggested for use on lighter soils and/or thosehaving a low organic matter content, for selective weed control or forsituations where only short-term persistence is required.

The compounds of the invention may be used in combination with any othercommercial herbicide examples of which are those of the triazine,triazole, uracil, urea, amide, diphenylether, carbamate and bipyridyliumtypes.

The herbicidal properties of the subject compounds were discovered in anumber of greenhouse tests. The test procedures and results follow.

Test A

Seeds of crabgrass (Digitaria spp.), barnyardgrass (Echinochloacrusgalli), wild oats (Avena fatua), sicklepod (Cassia obtusifolia),morningglory (Ipomoea spp.), cocklebur (Xanthium pensylvanicum),sorghum, corn, soybean, sugar beet, rice, wheat, and purple nutsedge(Cyperus rotundus) tubers were planted and treated preemergence with thetest chemicals dissolved in a non-phytotoxic solvent. At the same time,these crop and weed species, along with cotton and bush bean, weretreated with a soil/foliage application. At the time of treatment, theplants ranged in height from 2 to 18 cm. Treated plants and controlswere maintained in a greenhouse for sixteen days, after which allspecies were compared to controls and visually rated for response totreatment. The ratings, summarized in Table A, are based on a numericalscale extending from 0=no injury, to 10=complete kill. The accompanyingdescriptive symbols have the following meanings:

C=chlorosis/necrosis;

E=emergence inhibition;

G=growth retardation;

H=formative effect;

U=unusual pigmentation; and

6Y=abscised buds or flowers.

Note that compounds tested are highly active herbicides at the low ratesof application selected for this test. ##STR65##

                  TABLE A                                                         ______________________________________                                                  Cmpd. 1   Cmpd. 1   Cmpd. 2 Cmpd. 3                                 Rate kg/ha                                                                              .05       0.4       .05     .05                                     ______________________________________                                        POST-                                                                         EMERGENCE                                                                     Bush bean 3C,7H,6Y  9C        9C      9C                                      Cotton    5C,7H     6C,9G     4C,9G   3C,9G                                   Morningglory                                                                            3C        4C,8G     2C,9G   3C,8H                                   Cocklebur 3G        8G        3C,9G   3C,8H                                   Sicklepod 2C        3C,8G     2C,8G   4C,9G                                   Nutsedge  2C,6G     10C       4C,9G   9C                                      Crabgrass 0         2C,8G     1C,3H   2C,3G                                   Barnyardgrass                                                                           2C,6H     9C        5C,9H   2C,9H                                   Wild Oats 1C        1C,7G     0       2C,4G                                   Wheat     1C        1C,9G     0       3G                                      Corn      2U,8H     6U,9G     3U,9G   2U,9G                                   Soybean   1C,3H     4C,9G     2C,9H   3C,9H                                   Rice      2C,8H     5C,9G     3C,9G   4C,9G                                   Sorghum   1U,9G     5U,9G     2C,9G   2C,9G                                   Sugar beet                                                                              --        --        --      --                                      PRE-                                                                          EMERGENCE                                                                     Morningglory                                                                            3C        8G        9G      9G                                      Cocklebur 2C,7H     8H        9H      --                                      Sicklepod 2C,5G     3C,9G     2C,8G   9G                                      Nutsedge  5G        3C,9G     2C,5G   10E                                     Crabgrass 0         3C        1C,3G   1C,5G                                   Barnyardgrass                                                                           3C,6H     3C,9H     5C,9H   9H                                      Wild Oats 0         2C,7G     5C,9G   8G                                      Wheat     3G        2C,8G     4C,9G   2C,8G                                   Corn      2C,6G     1C,9G     2C,9G   2C,9H                                   Soybean   2C        3C,6G     3C,8H   7H                                      Rice      4C,6G     10E       5C,9G   10E                                     Sorghum   2C,7H     3C,9H     4C,9G   1C,9H                                   Sugar beet                                                                              --        --        --      --                                      ______________________________________                                                  Cmpd. 4   Cmpd. 5   Cmpd. 6 Cmpd. 7                                 Rate kg/ha                                                                              .05       .05       .05     0.5                                     ______________________________________                                        POST-                                                                         EMERGENCE                                                                     Bush bean 1C        5C,9G,6Y  3C,6H,6Y                                                                              9C                                      Cotton    4C,8G     4C,8H     2C,5G   6C,9G                                   Morningglory                                                                            3C,8G     3C,5G     3G      2C,7G                                   Cocklebur 2C        5G        4G      4C,9H                                   Sicklepod 5c,9G     1C        3G      9C                                      Nutsedge  0         3C,8G     7C,9G   10C                                     Crabgrass 3C        2H        10C     4C,9G                                   Barnyardgrass                                                                           2C,5H     3C,8H     4H      9C                                      Wild Oats 0         2C        0       5C,9H                                   Wheat     0         1C        0       5C,9G                                   Corn      2G        3C,8H     2C,8H   5C,9G                                   Soybean   3C,8G     2C,7H     2C,2H   5C,9G                                   Rice      3G        3C,9H     2C,8H   5C,9G                                   Sorghum   3G        3C,9G     2C,9H   4U,9G                                   Sugar beet                                                                              --        --        2C      10C                                     PRE-                                                                          EMERGENCE                                                                     Morningglory                                                                            9G        3C        2C,4G   8H                                      Cocklebur 9H        9H        9H      8H                                      Sicklepod 9G        3C,8H     2C,5G   2C,9G                                   Nutsedge  9G        3C,8G     2C,5G   10E                                     Crabgrass 3G        2C        1C      2C                                      Barnyardgrass                                                                           2C,5G     5C,9H     2H      4C,9H                                   Wild Oats 1C        2C,8G     2C,8G   3C,9G                                   Wheat     1C        3C,9G     9G      2C,9H                                   Corn      2C,8G     4C,9H     9G      3C,9H                                   Soybean   8H        3C,5H     4C,7G   3C,7H                                   Rice      6G        5C,9H     3C,8H   10E                                     Sorghum   2C,5G     4C,9H     2C,9H   2C,9G                                   Sugar beet                                                                              --        --        2C,9G   9C                                      ______________________________________                                                          Cmpd. 8     Cmpd. 9                                         Rate kg/ha        .05         .05                                             ______________________________________                                        POST-EMERGENCE                                                                Bush bean         5C,9G,6Y    5C,9G,6Y                                        Cotton            9C          --                                              Morningglory      5C,9G       5C,9G                                           Cocklebur         4C,9G       4C,9G                                           Sicklepod         3C,8G       4C,3H                                           Nutsedge          2C,7G       5G                                              Crabgrass         2C,9G       2C,8G                                           Barnyardgrass     2C,9H       5C,9H                                           Wild Oats         2C,8G       0                                               Wheat             5C,9G       0                                               Corn              3U,9H       9C                                              Soybean           2C,9H       9C                                              Rice              5C,9G       5C,9G                                           Sorghum           2C,9G       9C                                              Sugar beet        3C,9G       9C                                              PRE-EMERGENCE                                                                 Morningglory      9C          9C                                              Cocklebur         9H          --                                              Sicklepod         5C,9G       2C,9G                                           Nutsedge          10E         6G                                              Crabgrass         3C,9G       2C,6G                                           Barnyardgrass     4C,9H       3C,9H                                           Wild Oats         3C,9G       3C,9G                                           Wheat             10C         1C,6G                                           Corn              9G          5C,9H                                           Soybean           3C,9H       9H                                              Rice              10E         10E                                             Sorghum           5C,9H       5C,9H                                           Sugar beet        5C,9G       9C                                              ______________________________________                                    

Test B

Two plastic bulb pans were filled with fertilized and limed Woodstownsandy loam. One pan was planted with corn, sorghum, Kentucky bluegrassand several grass weeds. The other pan was planted with cotton,soybeans, purple nutsedge (Cyperus rotundus), and several broadleafweeds. The following grass and broadleaf weeds were planted: crabgrass(Digitaria sanguinalis), barnyardgrass (Echinochloa crusgalli), wildoats (Avena fatua), johnsongrass (Sorghum halepense), dallisgrass(Paspalum dilatatum), giant foxtail (Setaria faberii), cheatgrass(Bromus secalinus), mustard (Brassica arvensis), cocklebur (Xanthiumpensylvanicum), pigweed (Amaranthus retroflexus), morningglory (Ipomoeahederacea), sicklepod (Cassia obtusifolia), teaweed, (Sida spinosa),velvetleaf (Abutilon theophrasti), and jimsonweed (Datura stramonium). A12.5 cm diameter plastic pot was also filled with prepared soil andplanted with rice and wheat. Another 12.5 cm pot was planted with sugarbeets. The above four containers were treated preemergence with severaltest compounds within the scope of the invention.

Twenty-eight days after treatment, the plants were evaluated andvisually rated for response to the chemical treatments utilizing therating system described previously for Test A. The data are summarizedin Table B.

                  TABLE B                                                         ______________________________________                                        PRE-EMERGENCE ON                                                              WOODSTOWN SANDY LOAM                                                          ______________________________________                                                   Compound 1      Compound 2                                         Rate kg/ha   0.120    0.500    0.030  0.120                                   ______________________________________                                        Crabgrass    2G       5G       2G     4G                                      Barnyardgrass                                                                              8G,3H    10C      7G,3H  9G,5H                                   Sorghum      --       --       7G,5H  9G,5H                                   Wild Oats    2G       5G       4G     5G                                      Johnsongrass 5G,3H    8G,3H    4G,3H  6G,2H                                   Dallisgrass  6G       8G,5H    2G     4G                                      Giant foxtail                                                                              6G,5H    8G,5H    4G     6G,3H                                   Ky. bluegrass                                                                              8G,8C    10C      6G     7G                                      Cheatgrass   6G,3C    10C      8G,8C  8G,9C                                   Sugar beets  8G,8C    10C      8G,8C  10C                                     Corn         7G,5H    9G,8C    6G,3H  7G,3H                                   Mustard      9G,9C    10C      9G,8C  9G,9C                                   Cocklebur    6G       7G,3H    6G     5G                                      Pigweed      8G       10C      --     --                                      Nutsedge     7G       10E      7G     7G                                      Cotton       3G       8G       3G     5G,3H                                   Morningglory 0        6G,5H    4G     9G,5C                                   Sicklepod    6G       7G       7G     8G,3H                                   Teaweed      5G       8G,3H    5G     10C                                     Velvetleaf   6G,5H    9G,9C    5G,5H  8G,9C                                   Jimsonweed   6G       7G       7G     8G,8C                                   Soybean      3G       6G,5H    3G,3H  6G,5H                                   Rice         9G,9C    10C      7G,8C  10C                                     Wheat        4G       6G       0      4G                                      ______________________________________                                                   Compound 3      Compound 4                                         Rate kg/ha   0.030    0.120    0.007  0.030                                   ______________________________________                                        Crabgrass    0        6G       0      0                                       Barnyardgrass                                                                              6G,2H    8G,5H    0      3G                                      Sorghum      6G,3H    9G,5H    0      0                                       Wild Oats    3G       6G       0      0                                       Johnsongrass 4G,2H    7G,5H    0      0                                       Dallisgrass  0        5G       0      0                                       Giant foxtail                                                                              3G       7G,3H    0      0                                       Ky. bluegrass                                                                              5G,3H    7G,3H    4G     0                                       Cheatgrass   8G,8C    8G,9C    0      0                                       Sugar beets  10C      10C      6G     8G                                      Corn         5G,3H    7G,3H    2G     3G                                      Mustard      9G,5H    9G,9C    9G     9G,9C                                   Cocklebur    0        3G       0      2G                                      Pigweed      10E      10E      --     --                                      Nutsedge     9G,9E    10E      0      5G                                      Cotton       2G       4G       2G     5G                                      Morningglory 3G       3G       0      7G                                      Sicklepod    8G       8G       5G     6G                                      Teaweed      7G       8G       6G     9G                                      Velvetleaf   7G,5H    9G,8C    5G,5H  8G                                      Jimsonweed   5G       6G       0      4G                                      Soybean      3G       6G,5H    5G     8G                                      Rice         8G,8C    10E      0      5G                                      Wheat        2G       4G       0      0                                       ______________________________________                                                        Compound 5                                                    Rate kg/ha        0.030      0.120                                            ______________________________________                                        Crabgrass         0          0                                                Barnyardgrass     2G         3H,8G                                            Sorghum           2G         3H,8G                                            Wild Oats         0          2G                                               Johnsongrass      0          2H,4G                                            Dallisgrass       4G         8G                                               Giant foxtail     3H,4G      5H,8G                                            Ky. bluegrass     6G         10E                                              Cheatgrass        5G         8G                                               Sugar beets       5G         8G                                               Corn              3G         3H,7G                                            Mustard           9G,9C      9G,9C                                            Cocklebur         2G         2G                                               Pigweed           --         --                                               Nutsedge          2G         6G                                               Cotton            3G         5G                                               Morningglory      2G         2G                                               Sicklepod         2G         5G                                               Teaweed           0          0                                                Velvetleaf        0          5G                                               Jimsonweed        0          4G                                               Soybean           3G         3G                                               Rice              8G         9G,9C                                            Wheat             2G         3G                                               ______________________________________                                    

Test C

The test chemicals, dissolved in a non-phytotoxic solvent, were appliedin an overall spray to the foliage and surrounding soil of selectedplant species. One day after treatment, plants were checked for rapidburn injury. Approximately fourteen days after treatment all specieswere visually compared to untreated controls and rated for response totreatment. The rating system was as described previously for Test A. Thedata are presented in Table C.

All plant species were seeded in Woodstown sandy loam soil and grown ina greenhouse. The following species were grown in soil contained inplastic pots (25 cm diameter by 13 cm deep): soybeans, cotton, alfalfa,corn, rice, wheat, sorghum, velvetleaf (Abutilon theophrasti), sesbania(Sesbania exaltata), sicklepod (Cassia obtusifolia), morningglory(Ipomoea hederacea), jimsonweed (Datura stramonium), cocklebur (Xanthiumpensylvanicum), crabgrass (Digitaria spp.), nutsedge (Cyperus rotundus),barnyardgrass (Echinochloa crusgalli), giant foxtail (Setaria faberii),and wild oats (Avena fatua). The following species were grown in soil ina paper cup (12 cm diameter by 13 cm deep): sunflower, sugar beets, andrape. All plants were sprayed approximately 14 days after planting.Additional plant species, such as johnsongrass and field bindweed, aresometimes added to this test in order to evaluate unusual selectivity.

                  TABLE C                                                         ______________________________________                                        Over-the-Top Soil/Foliage Treatment                                                       Compound 2     Compound 5                                         Rate, kg/ha   0.015    0.004   0.06  0.015                                    ______________________________________                                        Soybeans      8G,6C    6G      3G    0                                        Velvetleaf    0        0       4G    0                                        Sesbania      0        --      0     0                                        Sicklepod     0        0       0     0                                        Cotton        3G       3G      3G    3G                                       Morningglory  2G       0       4G    3G                                       Alfalfa       7G       5G      4G    3G                                       Jimsonweed    3G       0       0     0                                        Cocklebur     0        --      2G    3G                                       Sunflower     2G       0       3G    1G                                       Rape          2G       0       5G    0                                        Sugar beets   2G       0       --    --                                       Corn          2G       0       1C    0                                        Crabgrass     4G       0       0     0                                        Rice          6G       2G      6G    6G                                       Nutsedge      0        0       0     0                                        Barnyardgrass 0        3G      0     0                                        Wheat         0        0       0     0                                        Giant Foxtail 2G       4G      0     0                                        Wild Oats     0        0       0     0                                        Sorghum       3G       5G      8G    6G                                       Johnsongrass  0        0       0     0                                        Field Bindweed                                                                              3G       0       0     0                                        ______________________________________                                    

Test D

Two ten-inch in diameter plastic pans lined with polyethylene linerswere filled with prepared Woodstown sandy loam soil. One pan was plantedwith seeds of wheat (Triticum aestivum), barley (Hordeum vulgare), wildoats (Avena fatua), downy brome (Bromus tectorum), cheatgrass (Bromussecalinus), blackgrass (Alopecurus myosuroides), annual bluegrass (Poaannua), green foxtail (Setaria viridis), quackgrass (Agropyron repens),Italian ryegrass (Lolium multiflorum) and ripgut brome (Bromus rigidus).The other pan was planted with seeds of Russian thistle (Salsola kali),tansy mustard (Descuraina pinnata), cleavers (Galium aparine), tumblemustard (Sisymbrium altissium), kochia (Kochia scoparia), shepherd'spurse (Capsella bursa-pastoris), Matricaria inodora, black nightshade(Solanum nigrum), yellow rocket (Barbarea vulgaris), rapeseed (Brassicanapus), and wild buckwheat (Polygonum convolvulus). The above two panswere treated preemergence. At the same time, two pans in which the aboveplant species were growing were treated postemergence. Plant height atthe time of treatment ranged from 1-15 cm depending on plant species.

The compounds applied were diluted with a nonphytotoxic solvent andsprayed over the top of the pans. An untreated control and asolvent-alone control were included for comparison. All treatments weremaintained in the greenhouse for 19-21 days at which time the treatmentswere compared to the controls and the effects visually rated. Therecorded data are presented in Table D. Some of the compounds testedhave utility for selective weed control in cereal crops such as wheatand barley.

                  TABLE D                                                         ______________________________________                                                  Compound 2                                                                    Pre-Emergence   Post-Emergence                                      Rate kg/ha  0.060    0.015    0.060  0.015                                    ______________________________________                                        wheat       7G       2G       6G     3G                                       barley      1C,7G    2G       6G     3G                                       wild oats   1C,7G    5G       5G     2G                                       downy brome 2C,9G    8G       8G     7G                                       cheatgrass  1C,9G    8G       8G     7G                                       blackgrass  2C,8G    7G       5G     3G                                       annual bluegrass                                                                          8G       7G       7G     3G                                       green foxtail                                                                             2C,8G    2C,4G    2C,8G  4G                                       quackgrass  9G       8G       8G     6G                                       Italian ryegrass                                                                          1C,8G    7G       4C,8G  7G                                       ripgut brome                                                                              8G       8G       2C,8G  7G                                       Russian thistle                                                                           2C,3G    2G       8C,8G  4C,5G                                    tansy mustard                                                                             2C,9G    9G       8C,8G  5C,7G                                    Galium aparine                                                                            6G       8G       7G     4G                                       tumble mustard                                                                            1C,8G    9G       10C    7G                                       kochia      7G       5G       3C,8G  4G                                       shepherd's purse                                                                          2C,9G    9G       4C,9G  7G                                       Matricaria inodora                                                                        7G       7G       8C,8G  2C,7G                                    black nightshade                                                                          8G       5G       6G     6G                                       yellow rocket                                                                             9G       8G       7G     5G                                       rapeseed    2C,9G    9G       10C    2C,8G                                    wild buckwheat                                                                            7G       6G       7G     4G                                       ______________________________________                                                  Compound 3                                                                    Pre-Emergence   Post-Emergence                                      Rate kg/ha  0.060    0.015    0.060  0.015                                    ______________________________________                                        wheat       3G       0        3G     0                                        barley      3G       0        5G     0                                        wild oats   5G       0        4G     0                                        downy brome 9G       8G       9G     7G                                       cheatgrass  2C,9G    7G       8G     6G                                       blackgrass  7G       6G       6G     3G                                       annual bluegrass                                                                          7G       6G       2C,8G  3G                                       green foxtail                                                                             2C,6G    3G       2C,6G  6G                                       quackgrass  9G       8G       8G     7G                                       Italian ryegrass                                                                          8G       8G       2C,8G  6G                                       ripgut brome                                                                              8G       6G       7G     6G                                       Russian thistle                                                                           1C,2G    0        8C,8G  0                                        tansy mustard                                                                             9G       9G       10C    9G                                       Galium aparine                                                                            10E      8G       6G     5G                                       tumble mustard                                                                            2C,9G    9G       10C    9G                                       kochia      8G       2C,5G    2C,8G  5G                                       shepherd's purse                                                                          9C,9G    9C,9G    10C    2C,8G                                    Matricaria inodora                                                                        8G       9G       8C,8G  8C,8G                                    black nightshade                                                                          6G       3G       7G     6G                                       yellow rocket                                                                             9G       7G       8C,8G  8C,8G                                    rapeseed    3C,9G    9G       10C    10C                                      wild buckwheat                                                                            6G       4G       2C,8G  7G                                       ______________________________________                                                  Compound 5                                                                    Pre-Emergence   Post-Emergence                                      Rate kg/ha  0.060    0.250    0.060  0.250                                    ______________________________________                                        wheat       1C,2G    5G       2G     7G                                       barley      6G       2C,8G    3G     7G                                       wild oats   5G       7G       3G     5G                                       downy brome 5G       8G       5G     6G                                       cheatgrass  6G       8G       5G     7G                                       blackgrass  5G       1C,7G    6G     2C,7G                                    annual bluegrass                                                                          6G       1C,8G    4G     3C,8G                                    green foxtail                                                                             0        2C,6G    0      2C,5G                                    quackgrass  4G       8G       2G     6G                                       Italian ryegrass                                                                          8G       2C,9G    2C,6G  2C,8G                                    ripgut brome                                                                              6G       1C,8G    5G     7G                                       Russian thistle                                                                           0        2C,5G    0      10C                                      tansy mustard                                                                             8G       2C,9G    5G     8G                                       Galium aparine                                                                            9G       10E      0      3G                                       tumble mustard                                                                            7G       9G       0      6G                                       kochia      --       --       --     0                                        shepherd's purse                                                                          2C,9G    10C      5G     10C                                      Matricaria inodora                                                                        8G       9G       3G     9G                                       black nightshade                                                                          0        5G       0      4G                                       yellow rocket                                                                             8G       9G       0      6G                                       rapeseed    2C,8G    9G       7G     9C,9G                                    wild buckwheat                                                                            0        6G       0      3G                                       ______________________________________                                    

What is claimed is:
 1. A compound having the formula ##STR66## wherein Ris H or CH₃ ;R" is C₁ -C₃ alkyl; L is ##STR67## R₅ is C₃ -C₄ alkyl, C₃-C₄ alkoxy, OCH₂ CH₂ OCH₃, F, Cl, Br, NO₂, CF₃, CO₂ R₁₉, SO₂ NR₂₀ R₂₁,SO₂ N(OCH₃)CH₃, OSO₂ R₂₂, S(O)_(n) R₂₃, WCF₃, WCHF₂, C₃ -C₄ alkenyloxy,C₃ -C₄ alkynyloxy, C₁ -C₂ alkyl substituted with OCH₃ or OCH₂ CH₃, C₆H₅, ##STR68## R₆ is H, F, Cl, Br, CF₃, CH₃, OCH₃, SCH₃ or OCF₂ H; R₈ isCH₃, CH₂ CH₃, OCH₃, OCH₂ CH₃, F, Cl, Br, SO₂ NR₂₀ R₂₁, SO₂ N(OCH₃)CH₃ orS(O)_(n) R₂₃ : R₉ is C₂ -C₃ alkyl, F, Cl, Br, NO₂, CO₂ R₁₉, SO₂ NR₂₀R₂₁, SO₂ N(OCH₃)CH₃ or S(O)_(n) R₂₃ ; R₁₀ is Cl, NO₂, CO₂ CH₃, CO₂ CH₂CH₃, SO₂ N(CH₃)₂, OSO₂ CH₃, SO₂ CH₃, SO₂ CH₂ CH₃, OCH₃ or OCH₂ CH₃ ; R₁₁is H, CH₃ or CH₂ CH₃ ; R₁₂ is H, CH₃ or CH₂ CH₃ ; R₁₃ is H or CH₃ ; R₁₄is H or CH₃ ; R₁₅ is H or CH₃ ; R₁₆ is CH₃ or CH₂ CH₃ ; R₁₇ is H or C₁-C₄ alkyl; R₁₈ is H or CH₃ ; R₁₉ is C₁ -C₄ alkyl, CH₂ CH₂ OCH₃, CH₂ CH₂Cl or CH₂ CH═CH₂ ; R₂₀ is C₁ -C₃ alkyl; R₂₁ is C₁ -C₃ alkyl; R₂₂ is C₁-C₃ alkyl or N(CH₃)₂ ; R₂₃ is C₁ -C₃ alkyl or CH₂ CH═CH₂ ; m is 0 or 1;n is 0 or 2; Q₁ is O, S, SO₂ or NR₁₇ ; Q₂ is O, S or NR₁₇ ; and W is O,S or SO₂ ; A is ##STR69## X is CH₃, OCH₃, OCH₂ CH₃, Cl, F, Br, OCF₂ H,CH₂ F or CF₃ ; Y is H, CH₃, OCH₃, OCH₂ CH₃, CH₂ OCH₃, CH₂ OCH₂ CH₃,N(CH₃)₂, CH₂ CH₃, CF₃, SCH₃, OCH₂ CH═CH₂, OCH₂ C.tbd.CH, OCH₂ CF₃, OCH₂CH₂ OCH₃, CH₂ SCH₃, OCF₂ H, SCF₂ H, CR₂₄ (QCH₃)₂, ##STR70## or CR₂₄(QCH₂ CH₃)₂ ; Q is O or S; R₂₄ is H or CH₃ ; Z is CH;provided that (1)the total number of carbon atoms of R₂₀ and R₂₁ is less than or equal tofour; (2) when m is l, then R₁₃ is H; (3) when L is L-17, then R₁₇ andR₁₈ are not simultaneously H; (4) when X is Cl, F or Br, then Z is CHand Y is OCH₃, OCH₂ CH₃, N(CH₃)₂ or OCF₂ H; (5) when X or Y is OCF₂ H,then Z is CH;provided that (1) when L is L-1, then R₅ is C₂ -C₄ alkyl,C₂ -C₄ alkoxy, OCH₂ CH₂ OCH₃, OSO₂ R₂₂, S(O)_(n) CH₂ CH═CH₂, WCF₂,WCHF₂, C₃ -C₄ alkenyloxy, C₃ -C₄ alkynyloxy, C₁ -C₂ alkyl substitutedwith OCH₃ or OCH₂ CH₃, ##STR71## (2) when L is L-3, then R₈ is SO₂ NR₂₀R₂₁, SO₂ N(OCH₃)CH₃ or SO₂ R₂₃ ; (3) when L is L-4, L-5 or L-6, then R₉is C₁ -C₃ alkyl, F, Cl, Br, NO₂, SO₂ NR₂₀ R₂₁, SO₂ N(OCH₃)CH₃ orS(O)_(n) R₂₃.
 2. A compound of claim 1 wherein R is H.
 3. A compositionsuitable for controlling the growth of undesired vegetation whichcomprises a herbicidally effective amount of a compound of claim 1 andat least one of the following: surfactant, solid or liquid diluent.
 4. Amethod for the control of undesired vegetation which comprises applyingto the locus of the undesired vegetation a herbicidally effective amountof a compound of claim 1.